tert-butyl N-((1S)-1-cyanoethyl)carbamate → (S)-N-(1-cyanoethyl)-4-decylbenzamide

HRID 2360344Notes

Reaction equation

HRID 2360344 reaction equation
[C:1]([C@@H:3]([NH:5][C:6](=[O:12])OC(C)(C)C)[CH3:4])#[N:2].[CH2:13]([C:23]1[CH:31]=[CH:30][C:26](C(O)=O)=[CH:25][CH:24]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[C:1]([C@@H:3]([NH:5][C:6](=[O:12])[C:26]1[CH:25]=[CH:24][C:23]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:31][CH:30]=1)[CH3:4])#[N:2]

Participants

3

Reactant 2

HCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamateHCID 123614764-Decylbenzoic acid

Product 1

HCID 67197682(S)-N-(1-cyanoethyl)-4-decylbenzamide

Procedure

General procedure D was used to deprotect 0.198 g (1.2 mmols) of 4. The product was immediately carried on using general procedure F and coupled to 1.2 mmols of 7. The title product was purified with flash chromatography using a solvent system of ethyl acetate and hexanes (1:3) to yield 0.2 g (0.63 mmols). 1H NMR (500 MHz, CDCl3) δ 7.23 (d, J=8.2, 2H), 6.94 (d, J=7.3, 1H), 5.19-5.11 (m, 1H), 2.66-2.60 (m, 2H), 1.64 (dd, J=2.0, 7.2, 2H), 1.59 (dd, J=5.9, 13.3, 2H), 1.30 (dd, J=18.9, 22.5, 13H), 0.88 (t, J=6.9, 3H). 13C NMR (126 MHz, CDCl3) δ 173.67, 166.98, 147.92, 147.35, 129.98, 128.73, 127.28, 119.51, 52.38, 48.45, 36.25, 35.86, 31.88, 31.16, 29.59, 29.56, 29.45, 29.31, 29.23, 22.67, 19.47, 18.62, 14.12.

Workup

  1. customThe title product was purified with flash chromatography
  2. customto yield 0.2 g (0.63 mmols)

Sources & evidence

ORD record
ord-0adf239736c3403ca9ab366856f41795
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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