Ethyl 3-chloro-3-oxopropionate → (S)-3-(2-benzyl-4-(3-cyclobutoxy-4-methoxyphenyl)piperazin-1-yl)-3-oxopropanoic acid

HRID 1423154Notes

Reaction equation

HRID 1423154 reaction equation
C([O:3][C:4](=[O:9])[CH2:5][C:6](Cl)=[O:7])C.[CH2:10]([C@@H:17]1[NH:22][CH2:21][CH2:20][N:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH:32]3[CH2:35][CH2:34][CH2:33]3)[CH:24]=2)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([C@H:17]1[CH2:18][N:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH:32]3[CH2:35][CH2:34][CH2:33]3)[CH:24]=2)[CH2:20][CH2:21][N:22]1[C:6](=[O:7])[CH2:5][C:4]([OH:3])=[O:9])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 58188985HCID 58188985, compound2×

Product 1

HCID 66828643(S)-3-(2-benzyl-4-(3-cyclobutoxy-4-methoxyphenyl)piperazin-1-yl)-3-oxopropanoic acid

Procedure

Prepared by the method outlined for Example 127 using chlorocarbonyl-acetic acid ethyl ester and 3(S)-benzyl-1-(3-cyclobutoxy-4-methoxy-phenyl)-piperazine (Example 7, Compound 95) as starting material. Product as an oil (25 mg, 65%). LC/MS (Method B) 2.56 min, [M+1]+ 439. Potency class A.

Workup

  1. customPrepared by the method
  2. customLC/MS (Method B) 2.56 min, [M+1]+ 439

Sources & evidence

ORD record
ord-f80b9c6b9006463baa200665e1a81152
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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