tert-butyl N-((1S)-1-cyanoethyl)carbamate → (S)-4-(3-(benzyloxy)benzyloxy)-N-(1-cyanoethyl)benzamide

HRID 1484089Notes

Reaction equation

HRID 1484089 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:35]=[CH:36][CH:37]=1)[CH2:24][O:25][C:26]1[CH:34]=[CH:33][C:29](C(O)=O)=[CH:28][CH:27]=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:35]=[CH:36][CH:37]=1)[CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([C:6]([NH:5][C@H:3]([C:1]#[N:2])[CH3:4])=[O:12])=[CH:33][CH:34]=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 669129754-(3-(Benzyloxy)benzyloxy)benzoic acid

Product 1

HCID 68182862(S)-4-(3-(benzyloxy)benzyloxy)-N-(1-cyanoethyl)benzamideYield 51.1%

Procedure

General procedures D and E were used to deprotect 0.45 mmols of (S)-tert-butyl 1-cyanoethylcarbamate and couple to 0.45 mmols of the acid 36. After purification by flash chromatography, 0.23 mmols of the title product was recovered. 1H NMR (500 MHz, CDCl3) δ 7.78-7.72 (m, 2H), 7.47-7.42 (m, 2H), 7.41-7.37 (m, 2H), 7.36-7.29 (m, 2H), 7.06 (s, 1H), 7.02 (s, 1H), 7.01-6.98 (m, 2H), 6.95 (dd, J=2.5, 8.2, 1H), 6.46 (s, 1H), 5.15 (dd, J=7.6, 14.9, 1H), 5.09 (s, 2H), 5.07 (s, 2H), 1.65 (d, J=7.2, 3H). 13C NMR (75 MHz, CDCl3) δ 191.04, 163.88, 159.36, 137.82, 136.98, 132.24, 130.09, 128.86, 128.29, 127.74, 120.05, 115.39, 114.79, 114.14, 70.25.

Sources & evidence

ORD record
ord-997ec4a598a947adb6a0f0c3a97e929b
Source dataset
uspto-grants-2016_08
Patent number
US09421177B2

Reaction notes

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