(RS)-alpha-(2-propenyl)-3,5-bis(trifluoromethyl)benzeneacetic acid → (RS)-N-(4-Oxo-1-phenylcyclohexyl)-alpha-(2-propenyl)-3,5-bis(trifluoromethyl)benzeneacetamide

HRID 852679Notes

Reaction equation

HRID 852679 reaction equation
[CH2:1]([CH:4]([C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=1)[C:5](O)=[O:6])[CH:2]=[CH2:3].Cl.[O:23]=[C:24]1[CH2:29][CH2:28][C:27]([NH2:36])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:26][CH2:25]1>>[O:23]=[C:24]1[CH2:25][CH2:26][C:27]([NH:36][C:5](=[O:6])[CH:4]([CH2:1][CH:2]=[CH2:3])[C:8]2[CH:13]=[C:12]([C:14]([F:15])([F:17])[F:16])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:28][CH2:29]1

Participants

3

Reactant 2

HCID 21955192(RS)-alpha-(2-propenyl)-3,5-bis(trifluoromethyl)benzeneacetic acidHCID 219552264-Oxo-1-phenylcyclohexylamine hydrochloride

Product 1

HCID 21955379(RS)-N-(4-Oxo-1-phenylcyclohexyl)-alpha-(2-propenyl)-3,5-bis(trifluoromethyl)benzeneacetamide

Procedure

Prepared from (RS)-α-(2-propenyl)-3,5-bis(trifluoromethyl)benzeneacetic acid (Description 9) and 4-oxo-1-phenylcyclohexylamine hydrochloride (Description 3) according to the method of Description 11. 1H NMR (400 MHz, CDCl3) δ 7.80 (1H, s), 7.73 (2H, s), 7.35-7.2 (5H, m), 5.80 (1H, br s), 5.75-5.63 (1H, m), 5.13-5.05 (2H, m), 3.56 (1H, dd, J 7, 6 Hz), 2.90-2.80 (21H, m), 2.65-2.55 (1H, m), and 2.52-2.30 (7H, m).

Sources & evidence

ORD record
ord-bb06209db3534aec984964ca11b84eac
Source dataset
uspto-grants-2007_08
Patent number
US07253205B2

Reaction notes

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