No renderable structure data available
CC(C)(C)OC(=O)NC(C(=O)O)C(C)(C)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-hydroxy-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid |
|---|---|
| IUPAC Name | — |
| CAS Number | 105504-72-1 |
| Database ID | 13756005 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-hydroxy-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid (CAS 105504-72-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 13756005
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a24ca881a9f546eabffe7cb6a1f4ec3dConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (1.0 g, 4.29 mmol) was dissolved in THF (14 mL) and cooled to 0° C. in an external ice/brine bath. MeI (2.13 mL, 34.3 mmol) was added at 0° C. Solid NaH (60% dispersion in mineral oil, 0.514 g, 12.87 mmol) was added slowly at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was diluted in ethyl acetate and water was added slowly with stirring. The quenched mixture was concentrated in vacuo and partitioned between diethyl ether and water. The ether layer was extracted with sodium bicarbonate twice. The combined bicarbonate layers were acidified with aqueous citric acid to pH 3 and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water, sodium thiosulfate, water, dried with sodium sulfate and concentrated to yield 2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid (0.99 g, 94%) as an oil. Upon completion of the addition the solution was removed from the ice bath to warm to room temperature the crude reaction mixture with stirring The quenched mixture was concentrated in vacuo partitioned between diethyl ether and water The ether layer was extracted with sodium bicarbonate twice extracted three times with ethyl acetate The combined ethyl acetate layers were washed with water, sodium thiosulfate, water dried with sodium sulfate concentrated
Source ID: ord-7040fb3fedba4f318c307d347856e056Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a24ca881a9f546eabffe7cb6a1f4ec3dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a24ca881a9f546eabffe7cb6a1f4ec3dConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (1.0 g, 4.29 mmol) was dissolved in THF (14 mL) and cooled to 0° C. in an external ice/brine bath. MeI (2.13 mL, 34.3 mmol) was added at 0° C. Solid NaH (60% dispersion in mineral oil, 0.514 g, 12.87 mmol) was added slowly at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was diluted in ethyl acetate and water was added slowly with stirring. The quenched mixture was concentrated in vacuo and partitioned between diethyl ether and water. The ether layer was extracted with sodium bicarbonate twice. The combined bicarbonate layers were acidified with aqueous citric acid to pH 3 and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water, sodium thiosulfate, water, dried with sodium sulfate and concentrated to yield 2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid (0.99 g, 94%) as an oil. Upon completion of the addition the solution was removed from the ice bath to warm to room temperature the crude reaction mixture with stirring The quenched mixture was concentrated in vacuo partitioned between diethyl ether and water The ether layer was extracted with sodium bicarbonate twice extracted three times with ethyl acetate The combined ethyl acetate layers were washed with water, sodium thiosulfate, water dried with sodium sulfate concentrated
Source ID: ord-7040fb3fedba4f318c307d347856e056Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (1.0 g, 4.29 mmol) was dissolved in THF (14 mL) and cooled to 0° C. in an external ice/brine bath. MeI (2.13 mL, 34.3 mmol) was added at 0° C. Solid NaH (60% dispersion in mineral oil, 0.514 g, 12.87 mmol) was added slowly at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was diluted in ethyl acetate and water was added slowly with stirring. The quenched mixture was concentrated in vacuo and partitioned between diethyl ether and water. The ether layer was extracted with sodium bicarbonate twice. The combined bicarbonate layers were acidified with aqueous citric acid to pH 3 and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water, sodium thiosulfate, water, dried with sodium sulfate and concentrated to yield 2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid (0.99 g, 94%) as an oil. Upon completion of the addition the solution was removed from the ice bath to warm to room temperature the crude reaction mixture with stirring The quenched mixture was concentrated in vacuo partitioned between diethyl ether and water The ether layer was extracted with sodium bicarbonate twice extracted three times with ethyl acetate The combined ethyl acetate layers were washed with water, sodium thiosulfate, water dried with sodium sulfate concentrated
Source ID: ord-f452e748a0c2478687d40f354aab511aConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (1.0 g, 4.29 mmol) was dissolved in THF (14 mL) and cooled to 0° C. in an external ice/brine bath. MeI (2.13 mL, 34.3 mmol) was added at 0° C. Solid NaH (60% dispersion in mineral oil, 0.514 g, 12.87 mmol) was added slowly at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was diluted in ethyl acetate and water was added slowly with stirring. The quenched mixture was concentrated in vacuo and partitioned between diethyl ether and water. The ether layer was extracted with sodium bicarbonate twice. The combined bicarbonate layers were acidified with aqueous citric acid to pH 3 and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water, sodium thiosulfate, water, dried with sodium sulfate and concentrated to yield 2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid (0.99 g, 94%) as an oil. Upon completion of the addition the solution was removed from the ice bath to warm to room temperature the crude reaction mixture with stirring The quenched mixture was concentrated in vacuo partitioned between diethyl ether and water The ether layer was extracted with sodium bicarbonate twice extracted three times with ethyl acetate The combined ethyl acetate layers were washed with water, sodium thiosulfate, water dried with sodium sulfate concentrated
Source ID: ord-ab11c9f7aed34eaeae7f5740ac701885Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (1.0 g, 4.29 mmol) was dissolved in THF (14 mL) and cooled to 0° C. in an external ice/brine bath. MeI (2.13 mL, 34.3 mmol) was added at 0° C. Solid NaH (60% dispersion in mineral oil, 0.514 g, 12.87 mmol) was added slowly at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was diluted in ethyl acetate and water was added slowly with stirring. The quenched mixture was concentrated in vacuo and partitioned between diethyl ether and water. The ether layer was extracted with sodium bicarbonate twice. The combined bicarbonate layers were acidified with aqueous citric acid to pH 3 and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water, sodium thiosulfate, water, dried with sodium sulfate and concentrated to yield 2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid (0.99 g, 94%) as an oil. Upon completion of the addition the solution was removed from the ice bath to warm to room temperature the crude reaction mixture with stirring The quenched mixture was concentrated in vacuo partitioned between diethyl ether and water The ether layer was extracted with sodium bicarbonate twice extracted three times with ethyl acetate The combined ethyl acetate layers were washed with water, sodium thiosulfate, water dried with sodium sulfate concentrated
Source ID: ord-da81f00557f4404f8aef2b7292413b3cConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (1.0 g, 4.29 mmol) was dissolved in THF (14 mL) and cooled to 0° C. in an external ice/brine bath. MeI (2.13 mL, 34.3 mmol) was added at 0° C. Solid NaH (60% dispersion in mineral oil, 0.514 g, 12.87 mmol) was added slowly at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was diluted in ethyl acetate and water was added slowly with stirring. The quenched mixture was concentrated in vacuo and partitioned between diethyl ether and water. The ether layer was extracted with sodium bicarbonate twice. The combined bicarbonate layers were acidified with aqueous citric acid to pH 3 and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water, sodium thiosulfate, water, dried with sodium sulfate and concentrated to yield 2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid (0.99 g, 94%) as an oil. Upon completion of the addition the solution was removed from the ice bath to warm to room temperature the crude reaction mixture with stirring The quenched mixture was concentrated in vacuo partitioned between diethyl ether and water The ether layer was extracted with sodium bicarbonate twice extracted three times with ethyl acetate The combined ethyl acetate layers were washed with water, sodium thiosulfate, water dried with sodium sulfate concentrated
Source ID: ord-db5f696c6e33465cbe4cbb21a7ef267bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was synthesized in analogy to Example 112e, using 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (CAN 105504-72-1) and methanamine hydrochloride as starting materials and isolated (486 mg, 38%); MS (ESI, m/z): 247.2 (M+H+). isolated (486 mg, 38%)
Source ID: ord-4d8a2040576f40389348dad3e3507555Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (1.0 g, 4.29 mmol) was dissolved in THF (14 mL) and cooled to 0° C. in an external ice/brine bath. MeI (2.13 mL, 34.3 mmol) was added at 0° C. Solid NaH (60% dispersion in mineral oil, 0.514 g, 12.87 mmol) was added slowly at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was diluted in ethyl acetate and water was added slowly with stirring. The quenched mixture was concentrated in vacuo and partitioned between diethyl ether and water. The ether layer was extracted with sodium bicarbonate twice. The combined bicarbonate layers were acidified with aqueous citric acid to pH 3 and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water, sodium thiosulfate, water, dried with sodium sulfate and concentrated to yield 2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid (0.99 g, 94%) as an oil. Upon completion of the addition the solution was removed from the ice bath to warm to room temperature the crude reaction mixture with stirring The quenched mixture was concentrated in vacuo partitioned between diethyl ether and water The ether layer was extracted with sodium bicarbonate twice extracted three times with ethyl acetate The combined ethyl acetate layers were washed with water, sodium thiosulfate, water dried with sodium sulfate concentrated
Source ID: ord-5dce4cca71a548aab5295fceadbd90f2Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (1.0 g, 4.29 mmol) was dissolved in THF (14 mL) and cooled to 0° C. in an external ice/brine bath. MeI (2.13 mL, 34.3 mmol) was added at 0° C. Solid NaH (60% dispersion in mineral oil, 0.514 g, 12.87 mmol) was added slowly at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was diluted in ethyl acetate and water was added slowly with stirring. The quenched mixture was concentrated in vacuo and partitioned between diethyl ether and water. The ether layer was extracted with sodium bicarbonate twice. The combined bicarbonate layers were acidified with aqueous citric acid to pH 3 and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water, sodium thiosulfate, water, dried with sodium sulfate and concentrated to yield 2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid (0.99 g, 94%) as an oil. Upon completion of the addition the solution was removed from the ice bath to warm to room temperature the crude reaction mixture with stirring The quenched mixture was concentrated in vacuo partitioned between diethyl ether and water The ether layer was extracted with sodium bicarbonate twice extracted three times with ethyl acetate The combined ethyl acetate layers were washed with water, sodium thiosulfate, water dried with sodium sulfate concentrated
Source ID: ord-7040fb3fedba4f318c307d347856e056PubChem References
These sources are listed in the compound's public database record.
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