HCID 58972242, compound → (2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(3,3-dimethylbutoxy)-morpholine-4-carboxylic acid tert-butyl ester

HRID 20337Notes

Reaction equation

HRID 20337 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([O:29]CC2C=CC=CC=2)[C@@H:15]([NH:25][C:26](=[O:28])[CH3:27])[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:12][O:11][C@H:10]([O:37][CH2:38][CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:9]1)=[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:29])[C@@H:15]([NH:25][C:26](=[O:28])[CH3:27])[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:12][O:11][C@@H:10]([O:37][CH2:38][CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 58972242HCID 58972242, compound

Product 1

HCID 68559571(2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(3,3-dimethylbutoxy)-morpholine-4-carboxylic acid tert-butyl esterYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Stir (2S,5R)-5-[(1S,2S)-2-Acetylamino-1-benzyloxy-3-(3,5-difluorophenyl)-propyl]-2-(3,3-dimethylbutoxy)-morpholine-4-carboxylic acid tert-butyl ester (0.18 g, 0.29 mmol) and 10% palladium on carbon (0.18 g) in ethanol (5 mL) under hydrogen at room temperature for 14 hours. Filter through Celite® and concentrate to give the title compound (0.148 g, 99.4% yield).

Workup

  1. filtrationFilter through Celite®
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-da9a87b8722e477f8f1243f4f570f7a3
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

Loading…