p-Octylbenzoic acid → (S)-N-(1-cyanoethyl)-4-octylbenzamide

HRID 2360342Notes

Reaction equation

HRID 2360342 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:29]=[CH:28][C:24](C(O)=O)=[CH:23][CH:22]=1)[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:24]1[CH:23]=[CH:22][C:21]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:29][CH:28]=1)[CH3:4])#[N:2]

Participants

3

Reactant 2

HCID 19147p-Octylbenzoic acidHCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamate

Product 1

HCID 46197326(S)-N-(1-cyanoethyl)-4-octylbenzamideYield 42.9%

Procedure

General procedure D was used to deprotect 2.8 mmols of 4 and immediately couple to 2.8 mmols of 2 using general procedure F. The product was purified using column chromatography using a solvent system of ethyl acetate and hexanes (1:3, Rf=0.5) to yield 0.340 g (1.2 mmols) of the desired product. 1H NMR (300 MHz, CDCl3) δ 7.71 (d, J=8.2, 2H), 7.23 (d, J=7.6, 2H), 6.75 (s, 1H), 5.27-5.06 (m, 1H), 2.71-2.55 (m, 2H), 1.64 (d, J=7.2, 2H), 1.61-1.53 (m, 1H), 1.35-1.13 (m, 10H), 0.87 (t, J=6.8, 3H). 13C NMR (126 MHz, CDCl3) δ 166.56, 147.99, 129.93, 128.81, 128.62, 127.18, 127.03, 119.40, 52.73, 48.54, 36.23, 35.86, 31.84, 31.22, 31.15, 29.41, 29.22, 22.64, 19.60, 18.71, 14.11.

Workup

  1. customThe product was purified

Sources & evidence

ORD record
ord-cc371c4d92fd410e945e75a0b9266618
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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