Dichloromethane → HCID 54015343, compound

HRID 266385Notes

Reaction equation

HRID 266385 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[C:13](O)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:29][CH:28]=1.ClCCl.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[C:13]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:31][CH:32]=2)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 225219p-Aminophenylacetic acid ethyl esterHCID 982211(2S)-2-[(4-chlorophenyl)sulfonylamino]-3-(1H-indol-3-yl)propanoic acid

Product 1

HCID 54015343HCID 54015343, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The procedure described in Example 180 was repeated, except that (S)-2-(4-chlorobenzenesulfonylamino)-3-(3-indolyl) propanoic acid (5 g) and ethyl 4-aminophenylacetate (2.36 g) were condensed in a mixed solvent of dichloromethane (100 ml) and acetonitrile (10 ml) in the presence of N,N'-dicyclohexylcarbodiimide (3.27 g). The reaction mixture was filtered, and the filtrate was concentrated. The resulting crude product was recrystallized from ethanol/acetonitrile (10/1) to obtain (S)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)-3-(3-indolyl)propanamide (4.86 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resulting crude product was recrystallized from ethanol/acetonitrile (10/1)

Sources & evidence

ORD record
ord-0ef78e9df0c641b3887f03a046663c54
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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