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

HRID 658549Notes

Reaction equation

HRID 658549 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[C:35]([CH3:36])=[CH:34][CH:33]=[CH:32][C:31]=1[Cl: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])[CH2:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[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 59804555N-tert-butyl-2-chloro-6-methyl-benzamide

Product 1

HCID 69109088[(R)-3-(2-tert-Butylcarbamoyl-3-chloro-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 (1.5 g, 4.6 mmol) and N-tert-butyl-2-chloro-6-methyl-benzamide (1.5 g, 4.6 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-7d8c9039a92a43d6903d87d479b9128b
Source dataset
uspto-grants-2011_12
Patent number
US08076514B2

Reaction notes

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