(2R,3S,5R)-5-[(1S,2S)-2-acetylamino-3-(3-benzyloxy-5-fluoro-phenyl)-1-hydroxy-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester → (2R,3S,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxypropyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester

HRID 20444Notes

Reaction equation

HRID 20444 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:36])[C@@H:15]([NH:32][C:33](=[O:35])[CH3:34])[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([O:24]CC3C=CC=CC=3)[CH:18]=2)[CH2:12][O:11][C@@H:10]([O:37][CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C@@H:9]1[CH3:43])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:36])[C@@H:15]([NH:32][C:33](=[O:35])[CH3:34])[CH2:16][C:17]2[CH:18]=[C:19]([OH:24])[CH:20]=[C:21]([F:23])[CH:22]=2)[CH2:12][O:11][C@@H:10]([O:37][CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C@@H:9]1[CH3:43])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 68561775(2R,3S,5R)-5-[(1S,2S)-2-acetylamino-3-(3-benzyloxy-5-fluoro-phenyl)-1-hydroxy-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 68560537(2R,3S,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxypropyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl esterYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Stir (2R,3S,5R)-5-[(1S,2S)-2-acetylamino-3-(3-benzyloxy-5-fluoro-phenyl)-1-hydroxy-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester (0.81 g, 1.34 mmol) and 10% palladium on carbon (0.50 g, 1.41 mmol) in ethanol (20 mL) under a hydrogen atmosphere for 3 hours. Filter and concentrate to give 0.652 g (94.7%) of the desired compound as a white solid.

Workup

  1. filtrationFilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-fa64f9f3a0154815880074c64d787898
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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