Dicyclohexylcarbodiimide → HCID 53837568, compound

HRID 266377Notes

Reaction equation

HRID 266377 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13](O)=[S:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][CH:26]=2)=[S:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 225219p-Aminophenylacetic acid ethyl esterHCID 178446059HCID 178446059, compound

Product 1

HCID 53837568HCID 53837568, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure described in Example 180 was repeated, except that (S)-2-(4-bromobenzenesulfonylamino)-4-ethylthiobutanoic acid (199 mg) and ethyl 4-aminophenylacetate (95.7 mg) were condensed in dichloromethane (2 ml) in the presence of N,N'-dicyclohexylcarbodiimide (139.1 mg). The reaction mixture was filtered, and the filtrate was concentrated. The resulting crude product was recrystallized from ethanol to obtain (S)-2-(4-bromobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)-4-ethylthiobutanamide (117.3 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resulting crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-2db21ddbe0a14a42b39f9bbfbef008db
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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