N-tert-butyl-2,4-dimethylbenzamide → [(R)-3-(2-tert-Butylcarbamoyl-5-methyl-phenyl)-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester

HRID 658540Notes

Reaction equation

HRID 658540 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]([C:19](=[O:24])N(OC)C)[CH2:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:11]=1[F:18])([CH3:4])([CH3:3])[CH3:2].[C:26]([NH:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=1[CH3:39])([CH3:29])([CH3:28])[CH3:27]>>[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([CH2:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:11]=1[F:18])[C:19](=[O:24])[CH2:39][C:33]1[CH:34]=[C:35]([CH3:38])[CH:36]=[CH:37][C:32]=1[C:31](=[O:40])[NH:30][C:26]([CH3:28])([CH3:27])[CH3:29])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 925378N-tert-butyl-2,4-dimethylbenzamideHCID 59804556[(R)-1-(Methoxy-methyl-carbamoyl)-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 69109488[(R)-3-(2-tert-Butylcarbamoyl-5-methyl-phenyl)-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester

Procedure

Using general procedure 2 with [(R)-1-(methoxy-methyl-carbamoyl)-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester (1.4 g, 4.1 mmol) and N-tert-Butyl-2,4-dimethyl-benzamide (2.5 g, 12 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-b460d5ee19fa470e9b151c1fe2df95da
Source dataset
uspto-grants-2011_12
Patent number
US08076514B2

Reaction notes

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