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

HRID 266376Notes

Reaction equation

HRID 266376 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13](O)=[S:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.N[C:22]1[CH:27]=[CH:26][C:25]([CH:28](C)[C:29]([O:31][CH3:32])=[O:30])=CC=1.C([N:36]([CH2:39][CH3:40])CC)C.[I-].[CH3:42][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][CH2:18][CH3:19])[C:13]([NH:36][C:39]2[CH:40]=[CH:42][C:26]([CH2:25][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:22]=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 178446879HCID 178446879, compound

Product 1

HCID 54278915(RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl)phenyl)-4-ethylthiobutanamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The procedure described in Example 177 was repeated, except that (RS)-2-(4-chlorobenzenesulfonylamino)-4-ethylthiobutanoic acid (1.0 g) and methyl 4-aminophenylpropionate hydrochloride (638.4 mg) were condensed in chloroform (30 ml) in the presence of triethylamine (1.4 ml) and 1-methyl-2-chloropyridinium iodide (907.5 mg) to obtain (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl)phenyl)-4-ethylthiobutanamide (374 mg).

Sources & evidence

ORD record
ord-58f35a1b842649e1bad0770aefcbe237
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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