(2R,3S,5R)-5-[(1S,2S)-1-hydroxy-2-acetylamino-3-(3-bromo-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester → (2R,3S,5R)-5-{(1S,2S)-2-Acetylamino-3-[3-fluoro-5-(3-methyl-butyl)-phenyl]-1-hydroxy-propyl}-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester

HRID 20462Notes

Reaction equation

HRID 20462 reaction equation
[Br-].[CH3:2][CH:3]([CH3:7])[CH2:4][CH2:5][Zn+].[C:8]([O:12][C:13]([N:15]1[C@@H:20]([C@@H:21]([OH:36])[C@@H:22]([NH:32][C:33](=[O:35])[CH3:34])[CH2:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[C:26](Br)[CH:25]=2)[CH2:19][O:18][C@@H:17]([O:37][CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C@@H:16]1[CH3:43])=[O:14])([CH3:11])([CH3:10])[CH3:9]>>[C:8]([O:12][C:13]([N:15]1[C@@H:20]([C@@H:21]([OH:36])[C@@H:22]([NH:32][C:33](=[O:35])[CH3:34])[CH2:23][C:24]2[CH:25]=[C:26]([CH2:5][CH2:4][CH:3]([CH3:7])[CH3:2])[CH:27]=[C:28]([F:30])[CH:29]=2)[CH2:19][O:18][C@@H:17]([O:37][CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C@@H:16]1[CH3:43])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 68561702(2R,3S,5R)-5-[(1S,2S)-1-hydroxy-2-acetylamino-3-(3-bromo-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl esterHCID 178445882HCID 178445882, compound

Product 1

HCID 68560172(2R,3S,5R)-5-{(1S,2S)-2-Acetylamino-3-[3-fluoro-5-(3-methyl-butyl)-phenyl]-1-hydroxy-propyl}-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl esterYield 78%

Procedure

Beginning with 3-methylbutyl zinc bromide and (2R,3S,5R)-5-[(1S,2S)-1-hydroxy-2-acetylamino-3-(3-bromo-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester (0.165 g, 0.287 mmol), the title compound (0.127 g, 78%) may be prepared essentially as described in Preparation 409.

Sources & evidence

ORD record
ord-ef9a4bf29eb5429b9b82e53f73b17f58
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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