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

HRID 266356Notes

Reaction equation

HRID 266356 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[ClH:24].N[C:26]1[CH:31]=[CH:30][C:29]([CH:32](C)[C:33]([O:35][CH3:36])=[O:34])=CC=1.C([N:40]([CH2:43][CH3:44])CC)C.[I-].[CH3:46][N+]1C=CC=CC=1Cl>C(Cl)(Cl)Cl>[Cl:24][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([NH:40][C:43]2[CH:44]=[CH:46][C:30]([CH2:29][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:26]=2)=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 15580485Methyl 2-(4-aminophenyl)propanoate hydrochlorideHCID 19032798(RS)-2-(4-chlorobenzenesulfonylamino)-4-phenylbutanoic acid

Product 1

HCID 19032887(RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl)phenyl)-4-phenylbutanamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The procedure described in Example 177 was repeated, except that (RS)-2-(4-chlorobenzenesulfonylamino)-4-phenylbutanoic acid (270.3 mg) and methyl 4-aminophenylpropionate hydrochloride (167.8 mg) were condensed in chloroform (10 ml) in the presence of triethylamine (360 μl) and 1-methyl-2-chloropyridinium iodide (243.2 mg), and then the resulting crude product was purified by column chromatography (silica gel 50 g, hexane/ethyl acetate=2/1) to obtain (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl)phenyl)-4-phenylbutanamide (43.2 mg) as a colorless oil.

Workup

  1. customthe resulting crude product was purified by column chromatography (silica gel 50 g, hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-0dc2491af4a644f9a33e064d169ee001
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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