[(R)-2-(2-fluoro-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester → [(R)-3-(2-tert-Butylcarbamoyl-5-fluoro-phenyl)-1-(2-fluoro-benzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester

HRID 658544Notes

Reaction equation

HRID 658544 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@@H:8]([C:17](=[O:22])N(OC)C)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16])([CH3:4])([CH3:3])[CH3:2].[C:24]([NH:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[CH3:37])([CH3:27])([CH3:26])[CH3:25]>>[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16])[C:17](=[O:22])[CH2:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[C:29](=[O:38])[NH:28][C:24]([CH3:26])([CH3:25])[CH3:27])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 59799859[(R)-2-(2-fluoro-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl esterHCID 59804558N-tert-Butyl-4-fluoro-2-methyl-benzamide

Product 1

HCID 69109421[(R)-3-(2-tert-Butylcarbamoyl-5-fluoro-phenyl)-1-(2-fluoro-benzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester

Procedure

Using general procedure 2 with [(R)-2-(2-Fluoro-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (1.6 g, 3.9 mmol) and N-tert-Butyl-4-fluoro-2-methyl-benzamide (3.0 g, 14 mmol) followed by purification by silica gel flash column chromatography gives the title compound.

Workup

  1. customfollowed by purification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-6021a916a0e34c7e92aa53ae10522517
Source dataset
uspto-grants-2011_12
Patent number
US08076514B2

Reaction notes

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