Dicyclohexylcarbodiimide → HCID 53735824, compound

HRID 266373Notes

Reaction equation

HRID 266373 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:16][CH2:17][CH3:18])[C:13](O)=[S:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24].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][CH3:18])[C:13]([NH:19][C:20]2[CH:30]=[CH:29][CH:28]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:21]=2)=[S:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11400Ethyl 3-aminobenzoateHCID 178448385HCID 178448385, compound

Product 1

HCID 53735824HCID 53735824, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure described in Example 180 was repeated, except that (S)-2-(4-bromobenzenesulfonylamino)-4-methylthiobutanoic acid (2.99 g) and ethyl 3-aminobenzoate (1.34 g) were condensed in dichloromethane (100 ml) in the presence of N,N'-dicyclohexylcarbodiimide (2.01 g). 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-(3-ethoxycarbonylphenyl)-4-methylthiobutanamide (2.018 g).

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-6dcbaa8a97ed446a8189d1455fe8e2d2
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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