tert-butyl N-((1S)-1-cyanoethyl)carbamate → HCID 67197134, compound

HRID 2360355Notes

Reaction equation

HRID 2360355 reaction equation
[C:1]([C@@H:3]([NH:5][C:6](=[O:12])OC(C)(C)C)[CH3:4])#[N:2].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=1)[O:18][C:19]1[CH:27]=[CH:26][C:22](C(O)=O)=[CH:21][CH:20]=1>>[C:1]([C@@H:3]([NH:5][C:6](=[O:12])[C:22]1[CH:21]=[CH:20][C:19]([O:18][C:17]2[CH:28]=[CH:29][CH:30]=[C:15]([O:14][CH3:13])[CH:16]=2)=[CH:27][CH:26]=1)[CH3:4])#[N:2]

Participants

3

Reactant 2

HCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamateHCID 20986778HCID 20986778, compound

Product 1

HCID 67197134HCID 67197134, compoundYield 46.8%

Procedure

General procedure D was used to deprotect 0.62 mmols of 4 and immediately coupled to 0.62 mmols of 28 using general procedure F. After flash chromatography, 0.29 mmols (0.087 g) of the title product was recovered. 1H NMR (500 MHz, CDCl3) δ 7.77 (d, J=8.9, 2H), 7.27 (dd, J=6.7, 9.6, 1H), 7.00 (d, J=8.9, 2H), 6.83 (d, J=8.0, 1H), 6.73 (dd, J=2.4, 8.3, 1H), 6.64-6.55 (m, 2H), 5.13 (dq, J=7.2, 14.5, 1H), 3.78 (s, 3H), 1.65 (d, J=7.2, 3H). 13C NMR (126 MHz, CDCl3) δ 166.03, 161.07, 156.72, 130.44, 129.26, 128.99, 126.89, 119.48, 117.83, 111.97, 110.17, 105.93, 77.29, 77.04, 76.78, 55.41, 36.33, 19.46, 18.59.

Sources & evidence

ORD record
ord-326de22eda474f179448b6037d7db76b
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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