No renderable structure data available
CC(C)(C)OC(=O)NCCC(=O)ON1C(=O)CCC1=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | (2,5-dioxopyrrolidin-1-yl) 3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 32703-87-0 |
| Database ID | 10684599 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
(2,5-dioxopyrrolidin-1-yl) 3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate (CAS 32703-87-0) 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 10684599
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-960f4839b14244d59625fe44099c0f7fConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f67046c06f2f46c4930f7ee045709daeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-Boc-β-Ala-OH (1 g, 5.29 nmol), N-hydroxysuccinimide (0.9 g, 7.82 mmol) in DMF (10 mL) were added HOBt (0.7 g, 5.25 mmol) and EDCI.HCl (1 g, 5.23 mmol) at 5° C. The reaction mixture was warmed to RT and stirred for 16 h. The progress of the reaction was monitored by TLC. The reaction was quenched with water and extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with water (3×100 mL), brine (150 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude compound was triturated with ether (2×25 mL) to afford N-Boc-β-Ala-OSu (1.1 g, crude) as white solid. 1H NMR (500 MHz, CDCl3): δ 5.10 (bs, 1H), 3.52 (q, J=6.0 Hz, 2H), 2.85-2.82 (m, 6H), 1.31 (s, 9H). The reaction was quenched with water extracted with ethyl acetate (2×150 mL) The combined organic layers were washed with water (3×100 mL), brine (150 mL) dried over anhydrous Na2SO4 concentrated under reduced pressure The crude compound was triturated with ether (2×25 mL)
Source ID: ord-da67826d218046bd93cebe57526ab382Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using 5.60 g of Boc-Asn-Leu-OEt and 5.60 g of Boc-β-Ala-OSu, the same procedure as in Reference Example 35 was repeated to obtain 4.71 g (yield: 70.6%) of the above objective compound having a melting point of 148°-153° C.
Source ID: ord-a5489522b48e4b6089e98f0a1c46a266Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl (5S)-5-amino-6-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-6-oxohexylcarbamate (1.60 g) and triethylamine (0.47 g) in chloroform (100 ml) was added N-[3-(tert-butoxycarbonylamino)propionyloxy]succinimide (1.34 g). The mixture was stirred at room temperature for 15 hours. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a crude product of tert-butyl (5S)-6-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-5-{[3-(tert-butoxycarbonylamino)propionyl]amino}-6-oxohexylcarbamate (2.09 g) as an oil. The crude product was used directly in the next step without further purification. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution The organic layer was dried over anhydrous magnesium sulfate filtered concentrated in vacuo
Source ID: ord-8584eb151e2445b59e4b6168d6f630cfConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl (5S)-5-amino-6-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-6-oxohexylcarbamate (1.60 g) and triethylamine (0.47 g) in chloroform (100 ml) was added N-[3-(tert-butoxycarbonylamino)propionyloxy]succinimide (1.34 g). The mixture was stirred at room temperature for 15 hours. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a crude product of tert-butyl (5S)-6-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-5-{[3-(tert-butoxycarbonylamino)propionyl]amino}-6-oxohexylcarbamate (2.09 g) as an oil. The crude product was used directly in the next step without further purification. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution The organic layer was dried over anhydrous magnesium sulfate filtered concentrated in vacuo
Source ID: ord-8584eb151e2445b59e4b6168d6f630cfConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl (4S)-4-amino-5-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-5-oxopentylcarbamate (4.90 g) and triethylamine (1.52 g) in chloroform (100 ml) was added N-[3-(tert-butoxycarbonylamino)propionyloxy]succinimide (4.26 g). The mixture was stirred at room temperature for 17 hours. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a crude product of tert-butyl (4S)-5-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-4-{[3-(tert-butoxycarbonylamino)propionyl]amino}-5-oxopentylcarbamate as an oil. The crude product was used directly in the next step without further purification. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution The organic layer was dried over anhydrous magnesium sulfate filtered concentrated in vacuo
Source ID: ord-b9784bd6f3144fc0b2dc164b8906c9bcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl (4S)-4-amino-5-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-5-oxopentylcarbamate (4.90 g) and triethylamine (1.52 g) in chloroform (100 ml) was added N-[3-(tert-butoxycarbonylamino)propionyloxy]succinimide (4.26 g). The mixture was stirred at room temperature for 17 hours. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a crude product of tert-butyl (4S)-5-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-4-{[3-(tert-butoxycarbonylamino)propionyl]amino}-5-oxopentylcarbamate as an oil. The crude product was used directly in the next step without further purification. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution The organic layer was dried over anhydrous magnesium sulfate filtered concentrated in vacuo
Source ID: ord-b9784bd6f3144fc0b2dc164b8906c9bcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-Boc-β-Ala-OH (1 g, 5.29 nmol), N-hydroxysuccinimide (0.9 g, 7.82 mmol) in DMF (10 mL) were added HOBt (0.7 g, 5.25 mmol) and EDCI.HCl (1 g, 5.23 mmol) at 5° C. The reaction mixture was warmed to RT and stirred for 16 h. The progress of the reaction was monitored by TLC. The reaction was quenched with water and extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with water (3×100 mL), brine (150 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude compound was triturated with ether (2×25 mL) to afford N-Boc-β-Ala-OSu (1.1 g, crude) as white solid. 1H NMR (500 MHz, CDCl3): δ 5.10 (bs, 1H), 3.52 (q, J=6.0 Hz, 2H), 2.85-2.82 (m, 6H), 1.31 (s, 9H). The reaction was quenched with water extracted with ethyl acetate (2×150 mL) The combined organic layers were washed with water (3×100 mL), brine (150 mL) dried over anhydrous Na2SO4 concentrated under reduced pressure The crude compound was triturated with ether (2×25 mL)
Source ID: ord-da67826d218046bd93cebe57526ab382Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using 5.60 g of Boc-Asn-Leu-OEt and 5.60 g of Boc-β-Ala-OSu, the same procedure as in Reference Example 35 was repeated to obtain 4.71 g (yield: 70.6%) of the above objective compound having a melting point of 148°-153° C.
Source ID: ord-a5489522b48e4b6089e98f0a1c46a266Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-960f4839b14244d59625fe44099c0f7fConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f67046c06f2f46c4930f7ee045709daePubChem References
These sources are listed in the compound's public database record.
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