Triethylamine → (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl)phenyl)-4-methylthiobutanamide

HRID 266370Notes

Reaction equation

HRID 266370 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH2:17][CH3:18])[C:13](O)=[S:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.N[C:21]1[CH:26]=[CH:25][C:24]([CH:27](C)[C:28]([O:30][CH3:31])=[O:29])=CC=1.C([N:35]([CH2:38][CH3:39])CC)C.[I-].[CH3:41][N+]1C=CC=CC=1Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH2:17][CH3:18])[C:13]([NH:35][C:38]2[CH:39]=[CH:41][C:25]([CH2:24][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:21]=2)=[S:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 15580485Methyl 2-(4-aminophenyl)propanoate hydrochlorideHCID 178449982HCID 178449982, compound

Product 1

HCID 54455701(RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl)phenyl)-4-methylthiobutanamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The procedure described in Example 177 was repeated, except that (RS)-2-(4-chlorobenzenesulfonylamino)-4-methylthiobutanoic acid (1.03 g) and methyl 4-aminophenylpropionate hydrochloride (617.4 mg) were condensed in chloroform (30 ml) in the presence of triethylamine (1.76 ml) and 1-methyl-2-chloropyridinium iodide (975.2 mg) to obtain as a colorless oil (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl)phenyl)-4-methylthiobutanamide (177.1 mg).

Sources & evidence

ORD record
ord-44ada0235d2b467bb5283ae81a2c8912
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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