Ethyl Acetate → (1S,2S,5R)-2-[(S)-1-(3-Chloro-2-fluoro-phenyl)-2-methoxy-ethylcarbamoyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

HRID 1527372Notes

Reaction equation

HRID 1527372 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]2[C@H:10]([CH2:11]2)[C@H:9]1[C:14](=[O:27])[NH:15][C@@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[F:26])[CH2:17][OH:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28]COC(C)=O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]2[C@H:10]([CH2:11]2)[C@H:9]1[C:14](=[O:27])[NH:15][C@@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[F:26])[CH2:17][O:18][CH3:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 68283613(1S,2S,5R)-2-[(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethylcarbamoyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Product 1

HCID 68284071(1S,2S,5R)-2-[(S)-1-(3-Chloro-2-fluoro-phenyl)-2-methoxy-ethylcarbamoyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Procedure

was prepared according to Scheme B9 (Step B) from (1S,2S,5R)-2-[(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethylcarbamoyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester. TLC, Rf (EtOAc): 0.65; MS (UPLC/MS): 413.4/415.4 [M+H]+, 457.4/459.4 [M+HCOO]−; tR (HPLC conditions a): 3.67 min.

Workup

  1. customwas prepared
  2. custom3.67 min.

Sources & evidence

ORD record
ord-d4cfc1b9d55b4a7392005bac2eb8ad8d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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