No renderable structure data available
CC(C)(C)OC(=O)C[N+]#[C-]Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl 2-isocyanoacetate |
|---|---|
| IUPAC Name | — |
| CAS Number | 2769-72-4 |
| Database ID | 2759404 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl 2-isocyanoacetate (CAS 2769-72-4) 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 2759404
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:; See reaction.notes.procedure_details.
Procedure: M.p. 176°-177° C., from 3-methyl-2-quinoxalinol and tert-butyl isocyanoacetate. (Compound 6)
Source ID: ord-f8dc19c0b03e4d9c880901d8026b548eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: M.p. 187°-190° C., from 2-quinoxalinol and tert-butyl isocyanoacetate. (Compound 4)
Source ID: ord-661450db4b474366839fc454e2dfdeccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1 ml of an approximately 2 molar solution of butyllithium in hexane is added over a period of 15 minutes to a solution, cooled to -10° C., of 282 mg (2 mmols) of isocyanoacetic acid tert.-butyl ester in 3 ml of dry hexane (distilled over sodium), whilst stirring vigorously and in a nitrogen atmosphere. The suspension which forms is stirred for a further 10 minutes and a solution of 413 μl (2 mmols) of diethyl phosphorochloridate in 5 ml of dry hexane is then added over a period of 15 minutes. The reaction mixture is stirred for a further 30 minutes, then treated with 20 ml of benzene and 5 ml of water and stirred vigorously for a further 10 minutes. The organic phase is washed with 3 times 5 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated in vacuo. The residue is chromatographed on silica gel. Benzene/ethyl acetate, 3:1, elutes diethylphosphono-isocyanoacetic acid tert.-butyl ester as a pale yellow oil; IR spectrum (in methylene chloride): characteristic bands at 3.4; 4.64; 5.70; 7.30; 8.00; 8.70 and 9.80μ. The suspension which forms is stirred for a further 10 minutes The reaction mixture is stirred for a further 30 minutes stirred vigorously for a further 10 minutes The organic phase is washed with 3 times 5 ml of saturated aqueous sodium chloride solution dried over sodium sulphate evaporated in vacuo The residue is chromatographed on silica gel
Source ID: ord-d1598b234bdc4ceda7ce8db8a4285bdcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of EXAMPLE 30 and making non-critical variations but starting with (S)-3,3a-dihydropyrrolo[1,2-a]quinoxaline-1,4(2H,5H)-dione (intermediate formed in EXAMPLE 282, 0.638 g) and tert-butyl isocyanoacetate (0.621 g), the title compound is obtained, mp 202°-207° (decomp); MS (m/z) at 325; IR (mineral oil) 1719, 1363, 1700, 1507, 1161, 1293 cm-1 ; NMR (CDCl3) 1.64, 2.25-2.40, 2.55-2.81, 3.31-3.41, 5.26, 7.23-7.29, 7.33, 7.52, 8.06, 8.34 δ; [α]D =-248° (0.96, methanol).
Source ID: ord-04913cf4be094362a6920062d0d2ca05Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure for EXAMPLE 30 and making non-critical variation but starting with 6-fiuoro-1,2,3,4-tetrahydro-3,3-dimethyl-4-[(pyrrolidino)carbonyl]quinoxalin-2-one (XXXII, EXAMPLE 32, 0.750 g) and t-butyl isocyanoacetate (0.436 g) are converted to the title compound. After crystallization from ethyl ether/hexane, mp 168.5°-169.5°; MS (m/z) at 414; IR (mineral oil) 1713, 1668, 1520, 1181 and 1155 cm-1 ; NMR (CDCl3) 1.63, 1.8, 1.92, 2.08, 2.95, 3.23, 3.58, 6.52, 6.71 and 7.92 δ.
Source ID: ord-32f9b82f6fd94687b647ee031b5696deConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of EXAMPLE 30 and making non-critical variations but starting with (S)-3,3a-dihydropyrrolo[1,2-a]quinoxaline-1,4(2H,5H)-dione (intermediate formed in EXAMPLE 282, 0.638 g) and tert-butyl isocyanoacetate (0.621 g), the title compound is obtained, mp 202°-207° (decomp); MS (m/z) at 325; IR (mineral oil) 1719, 1363, 1700, 1507, 1161, 1293 cm-1 ; NMR (CDCl3) 1.64, 2.25-2.40, 2.55-2.81, 3.31-3.41, 5.26, 7.23-7.29, 7.33, 7.52, 8.06, 8.34 δ; [α]D =-248° (0.96, methanol).
Source ID: ord-95a507efde8f4eee9a51c1e9992bee1aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure for EXAMPLE 30 and making non-critical variation but starting with 6-fluoro-1,2,3,4-tetrahydro-3,3-dimethyl-4-[(pyrrolidino)carbonyl]quinoxalin-2-one (XXXII, EXAMPLE 32, 0.750 g) and t-butyl isocyanoacetate (0.436 g) are converted to the title compound. After crystallization from ethyl ether/hexane, mp 168.5°-169.5°; MS (m/z) at 414; IR (mineral oil) 1713, 1668, 1520, 1181 and 1155 cm-1 ; NMR (CDCl3) 1.63, 1.8, 1.92, 2.08, 2.95, 3.23, 3.58, 6.52, 6.71 and 7.92 δ.
Source ID: ord-90a3bd1279bd4615b16096827d832b1aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium tert-butoxide (1M, 3.8 ml) is added to 5-fluoro-1,2,3,4-tetrahydro-4-[(pyrrolidino)carbonyl]quinoxalin-2-one (XXXII, EXAMPLE 29, 0.908 g) at 0° in THF (20 ml). The mixture is stirred for 30 min and then diethylchlorophosphate (0.55 ml) is added. The reaction is stirred for 1 hr at 0°, then cooled at -78°. tert-butyl isocyanoacetate (0.58 g) is added, followed by potassium tert-butoxide (1 M, 4.14 ml). The reaction is stirred at -78° for 4 hr, then allowed to warm to 20°-25° over 1 hr. The mixture is then partitioned between ethyl acetate, water, and saline. The organic layers are dried over magnesium sulfate and concentrated. The crude product is chromatographed on silica gel (250 ml) eluting with a gradient of ethyl acetate/dichloromethane (20/80 to 40/60). The appropriate fractions are pooled, concentrated and crystallized from dichloromethane/hexane to give the title compound; mp 213.5-214.5°; MS (m/z) at 386; IR (mineral oil) 1689, 1677, 1217, 1363 and 1157 cm-1 ; NMR (CDCl3) 1.63, 1.88, 3.36, 5.08, 7.08, 7.20, 7.33 and 8.00 δ. The reaction is stirred for 1 hr at 0° cooled at -78° The reaction is stirred at -78° for 4 hr to warm to 20°-25° over 1 hr The mixture is then partitioned between ethyl acetate, water, and saline The organic layers are dried over magnesium sulfate concentrated The crude product is chromatographed on silica gel (250 ml) eluting with a gradient of ethyl acetate/dichloromethane (20/80 to 40/60) concentrated crystallized from dichloromethane/hexane
Source ID: ord-93d1938e5a284794adfefb6c5f985fa4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure of EXAMPLE 30 and making non-critical variations but starting with (S)-3,3a-dihydropyrrolo[1,2-a]quinoxaline-1,4(2H,5H)-dione (intermediate formed in EXAMPLE 282, 0.638 g) and tert-butyl isocyanoacetate (0.621 g), the title compound is obtained, mp 202°-207° (decomp); MS (m/z) at 325; IR (mineral oil) 1719, 1363, 1700, 1507, 1161, 1293 cm-1 ; NMR (CDCl3) 1.64, 2.25-2.40, 2.55-2.81, 3.31-3.41, 5.26, 7.23-7.29, 7.33, 7.52, 8.06, 8.34 δ; [α]D =-248° (0.96, methanol).
Source ID: ord-cb68732d711c4d9ea5842cc9ca62370bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general procedure for EXAMPLE 30 and making non-critical variation but starting with 6-fluoro-1,2,3,4-tetrahydro-3,3-dimethyl-4-[(pyrrolidino)carbonyl]quinoxalin-2-one (XXXII, EXAMPLE 32, 0.750 g) and t-butyl isocyanoacetate (0.436 g) are converted to the title compound. After crystallization from ethyl ether/hexane, mp 168.5°-169.5°; MS (m/z) at 414; IR (mineral oil) 1713, 1668, 1520, 1181 and 1155 cm-1 ; NMR (CDCl3) 1.63, 1.8, 1.92, 2.08, 2.95, 3.23, 3.58, 6.52, 6.71 and 7.92 δ.
Source ID: ord-2889d2b5ed2642228305a27abebb2ba3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium tert-butoxide (1M, 3.8 ml) is added to 5-fluoro-1,2,3,4-tetrahydro-4-[(pyrrolidino)carbonyl]quinoxalin-2-one (XXXII, EXAMPLE 29, 0.908 g) at 0° in THF (20 ml). The mixture is stirred for 30 min and then diethylchlorophosphate (0.55 ml) is added. The reaction is stirred for 1 hr at 0°, then cooled at -78°. tert-butyl isocyanoacetate (0.58 g) is added, followed by potassium tert-butoxide (1M, 4.14 ml). The reaction is stirred at -78° for 4 hr, then allowed to warm to 20°-25° over 1 hr. The mixture is then partitioned between ethyl acetate, water, and saline. The organic layers are dried over magnesium sulfate and concentrated. The crude product is chromatographed on silica gel (250 ml) eluting with a gradient of ethyl acetate/dichloromethane (20/80 to 40/60). The appropriate fractions are pooled, concentrated and crystallized from dichloromethane/hexane to give the title compound; mp 213.5°-214.5°; MS (m/z) at 386; IR (mineral oil) 1689, 1677, 1217, 1363 and 1157 cm-1 ; NMR (CDCl3) 1.63, 1.88, 3.36, 5.08, 7.08, 7.20, 7.33 and 8.00 δ. The reaction is stirred for 1 hr at 0° cooled at -78° The reaction is stirred at -78° for 4 hr to warm to 20°-25° over 1 hr The mixture is then partitioned between ethyl acetate, water, and saline The organic layers are dried over magnesium sulfate concentrated The crude product is chromatographed on silica gel (250 ml) eluting with a gradient of ethyl acetate/dichloromethane (20/80 to 40/60) concentrated crystallized from dichloromethane/hexane
Source ID: ord-10e7e410975a4003933012be8b905ca8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: M.p. 176°-177° C., from 3-methyl-2-quinoxalinol and tert-butyl isocyanoacetate. (Compound 6)
Source ID: ord-f8dc19c0b03e4d9c880901d8026b548ePubChem References
These sources are listed in the compound's public database record.
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