4-(Octyloxy)benzoic acid → (S)-N-(1-cyanoethyl)-4-(octyloxy)benzamide

HRID 1484085Notes

Reaction equation

[C:1]([C@@H:3]([NH:5][C:6](=[O:12])OC(C)(C)C)[CH3:4])#[N:2].[CH2:13]([O:21][C:22]1[CH:30]=[CH:29][C:25](C(O)=O)=[CH:24][CH:23]=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:25]1[CH:29]=[CH:30][C:22]([O:21][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:23][CH:24]=1)[CH3:4])#[N:2]

Participants

Reactant 2

HCID 172314-(Octyloxy)benzoic acid

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

Product 1

HCID 68182863(S)-N-(1-cyanoethyl)-4-(octyloxy)benzamideYield 29.9%

Procedure

General procedure D and E were used to deprotect 1.17 mmols of (S)-tert-butyl 1-cyanoethylcarbamate and couple the resulting amine to 1.17 mmols of 31. After standard purification techniques 0.35 mmols of the title product were recovered. 1H NMR (500 MHz, CDCl3) δ 7.74 (d, J=8.9, 2H), 6.90 (d, J=8.8, 2H), 6.67 (s, 1H), 5.30-5.05 (m, 1H), 3.98 (t, J=6.6, 2H), 1.85-1.74 (m, 2H), 1.64 (d, J=7.2, 3H), 1.45 (s, 3H), 1.30 (d, J=19.1, 7H), 0.88 (t, J=6.9, 3H). 13C NMR (126 MHz, CDCl3) δ 166.26, 162.49, 129.11, 124.52, 119.58, 114.40, 68.26, 36.25, 31.77, 29.30, 29.19, 29.07, 25.95, 22.63, 19.53, 14.08.

Sources & evidence

ORD record: ord-df23f89a839e44b3bcd9729a59926385
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09421177B2

Reaction notes

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