tert-butyl N-((1S)-1-cyanoethyl)carbamate → HCID 67197801, compound

HRID 2360359Notes

Reaction equation

HRID 2360359 reaction equation
[C:1]([C@@H:3]([NH:5][C:6](=[O:12])OC(C)(C)C)[CH3:4])#[N:2].[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([CH:34]=[CH:35][CH:36]=1)[O:24][C:25]1[CH:33]=[CH:32][C:28](C(O)=O)=[CH:27][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([CH:34]=[CH:35][CH:36]=1)[O:24][C:25]1[CH:26]=[CH:27][C:28]([C:6]([NH:5][C@H:3]([C:1]#[N:2])[CH3:4])=[O:12])=[CH:32][CH:33]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamateHCID 67198964HCID 67198964, compound

Product 1

HCID 67197801HCID 67197801, compoundYield 38.5%

Procedure

General procedure D was used to deprotect 0.65 mmol of 4 and immediately coupled to 0.975 mmol of 40. After flash chromatography 0.96 g (0.25 mmol) of the title product was recovered. 1H NMR (300 MHz, CDCl3) δ 7.76 (d, J=8.8, 2H), 7.49-7.21 (m, 6H), 7.00 (d, J=8.7, 2H), 6.80 (d, J=8.3, 1H), 6.65 (d, J=12.0, 3H), 5.22-5.08 (m, 1H), 5.03 (s, 2H), 1.65 (d, J=7.2, 3H).

Sources & evidence

ORD record
ord-3bee5ae6d8c143f188e55fcf11276e26
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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