tert-butyl N-((1S)-1-cyanoethyl)carbamate → HCID 67198248, compound

HRID 2360356Notes

Reaction equation

[C:1]([C@@H:3]([NH:5][C:6](=[O:12])OC(C)(C)C)[CH3:4])#[N:2].[CH2:13]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)C(O)=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[C:1]([C@@H:3]([NH:5][C:6](=[O:12])[C:28]1[CH:27]=[CH:23][CH:22]=[C:21]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:29]=1)[CH3:4])#[N:2]

Participants

Reactant 2

HCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamate

HCID 53899176HCID 53899176, compound

Product 1

HCID 67198248HCID 67198248, compoundYield 34.8%

Procedure

General procedure D was used to deprotect 1.15 mmol of 4 and was then immediately coupled to 1.15 mmol of 35. After flash chromatography 0.115 g (0.4 mmol) of the title product was recovered. 1H NMR (500 MHz, CDCl3) δ 7.68-7.55 (m, 2H), 7.34 (dd, J=2.9, 9.5, 2H), 6.73 (d, J=7.7, 1H), 5.16 (p, J=7.2, 1H), 2.63 (t, J=7.7, 2H), 1.66 (d, J=7.2, 2H), 1.61 (s, 2H), 1.30 (dd, J=21.4, 28.1, 10H), 0.87 (t, J=7.0, 3H). 13C NMR (126 MHz, CDCl3) δ 166.89, 143.81, 143.59, 132.58, 132.52, 128.60, 127.34, 124.32, 119.40, 52.60, 48.47, 36.28, 35.81, 31.86, 31.43, 31.38, 29.42, 29.27, 29.23, 22.66, 19.54, 18.65, 14.11.

Sources & evidence

ORD record: ord-b893ed64d0044a1087966ae651cff982
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686046B2

Reaction notes

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