Ethyl Acetate → (2S,4R)-2-[(S)-1-(3-Chloro-2-fluoro-phenyl)-2-methoxy-ethylcarbamoyl]-4-fluoro-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1527370Notes

Reaction equation

HRID 1527370 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:14])([CH3:13])[CH2:10][C@H:9]1[C:15](=[O:28])[NH:16][C@@H:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[F:27])[CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29]COC(C)=O>>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:14])([CH3:13])[CH2:10][C@H:9]1[C:15](=[O:28])[NH:16][C@@H:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[F:27])[CH2:18][O:19][CH3:29])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 68283867(2S,4R)-2-[(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethylcarbamoyl]-4-fluoro-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68284566(2S,4R)-2-[(S)-1-(3-Chloro-2-fluoro-phenyl)-2-methoxy-ethylcarbamoyl]-4-fluoro-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

was prepared according to Scheme B9 (Step B) from (2S,4R)-2-[(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethylcarbamoyl]-4-fluoro-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester. TLC, Rf (EtOAc)=0.90; MS (UPLC-MS): 433.4/435.4 [M+H]+, 477.4 [M+HCOO]−; tR (HPLC conditions a): 3.73 min.

Workup

  1. customwas prepared
  2. custom3.73 min.

Sources & evidence

ORD record
ord-8fbdf827b6a446f1a3928324bd32449c
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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