HCID 68562017, compound → HCID 68562765, compound

HRID 20378Notes

Reaction equation

HRID 20378 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]([CH2:48][O:49]CC2C=CC=CC=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(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]([CH2:48][OH:49])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 68562017HCID 68562017, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68562765HCID 68562765, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Dissolve (1S,2S)-5-(R)-[1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(R)-benzyloxymethylmorpholine-4-carboxylic acid tert-butyl ester (4.750 g, 6.226 mmol) in ethanol (63 mL) and add 20% palladium hydroxide on carbon (4.750 g). Stir under one atmosphere of hydrogen gas for 42 hours, flush with nitrogen, dilute slurry with ethanol (175 mL), filter through a filtering agent, wash with ethanol and concentrate to give the desired compound (2.213 g, 88.3%).

Workup

  1. customflush with nitrogen
  2. additiondilute slurry with ethanol (175 mL)
  3. filtrationfilter through a filtering agent
  4. washwash with ethanol
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-9dc7078e5fd8451db8984b61f040c6a9
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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