(2R,3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester → HCID 68561942, compound

HRID 20416Notes

Reaction equation

HRID 20416 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([O:40]CC2C=CC=CC=2)[C@@H:15]([N:25](CC2C=CC=CC=2)CC2C=CC=CC=2)[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:48][CH2:49][C:50]([CH3:53])([CH3:52])[CH3:51])[C@@H:9]1[CH3:54])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:40])[C@@H:15]([NH2:25])[CH2:16][C:17]2[CH:18]=[C:19]([F:24])[CH:20]=[C:21]([F:23])[CH:22]=2)[CH2:12][O:11][C@@H:10]([O:48][CH2:49][C:50]([CH3:53])([CH3:52])[CH3:51])[C@@H:9]1[CH3:54])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 68562066(2R,3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 68561942HCID 68561942, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Stir (2R,3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester (645 mg, 0.87 mmol) and 20% palladium hydroxide on carbon (60% moisture, 645 mg) in ethyl acetate (10 mL) under one-atmosphere of hydrogen gas at room temperature overnight. Filter the suspension through a pad of filtering agent, wash with ethyl acetate and concentrate to give the desired compound (400 mg, 97%).

Workup

  1. filtrationFilter the suspension through a pad
  2. filtrationof filtering agent
  3. washwash with ethyl acetate
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-e3f9ed12ef2c464aae73ca7c67894b7e
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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