1,2-Dichloroethane → N-(2-ACETYLTHIOMETHYL-3-PHENYLPROPANOYL)-beta-(2-NAPHTHYL)-beta-ALANINE METHYL ESTER

HRID 1587985Notes

Reaction equation

HRID 1587985 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:18])[CH2:5][CH:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[NH2:7].[C:19]([S:22][CH2:23][CH:24]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:25](O)=[O:26])(=[O:21])[CH3:20].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(N(CC)CC)C>[CH3:2][O:3][C:4](=[O:18])[CH2:5][CH:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[NH:7][C:25](=[O:26])[CH:24]([CH2:23][S:22][C:19](=[O:21])[CH3:20])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 69893349Methyl 3-amino-3-(naphthalen-2-yl)propanoate hydrochloride

Product 1

HCID 86746977N-(2-ACETYLTHIOMETHYL-3-PHENYLPROPANOYL)-beta-(2-NAPHTHYL)-beta-ALANINE METHYL ESTER

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Mix equimolar parts of β-(2-naphthyl)-β-alanine methyl ester, hydrochloride and 2-acetylthiomethyl-3-phenylpropanoic acid with 1.2 equivalents each of EDC, triethylamine and HOBT in DMF and stir overnight. Evaporate the solvent, partition between EtOAc and water, and concentrate the organic layer. Separate on silica using ether/hexane and crystallize from acetone/hexane to obtain the title compound, m.p. 133°-135° C.

Workup

  1. customEvaporate the solvent
  2. custompartition between EtOAc and water
  3. concentrationconcentrate the organic layer
  4. customSeparate on silica
  5. customcrystallize from acetone/hexane

Sources & evidence

ORD record
ord-9594af5482e243e583c9b61ecf3b47ec
Source dataset
uspto-grants-1993_06
Patent number
US05219886

Reaction notes

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