HCID 57948096, compound → HCID 57948244, compound

HRID 340999Notes

Reaction equation

HRID 340999 reaction equation
[C:1]([O:5][C:6](=[O:32])[N:7]([CH2:12][C@H:13]([N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:24])[CH2:14][O:15]CC1C=CC=CC=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.CC(O)=O.[Pd]>[C:1]([O:5][C:6](=[O:32])[N:7]([CH2:12][C@H:13]([N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:24])[CH2:14][OH:15])[CH2:8][CH:9]([F:10])[F:11])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 57948096HCID 57948096, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57948244HCID 57948244, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of [(S)-3-Benzyloxy-2-(tert-butoxycarbonyl-methyl-amino)-propyl]-(2,2-difluoro-ethyl)-carbamic acid tert-butyl ester (2.42 g, 5.28 mmol) in MeOH (20 mL) and AcOH (2.0 mL) was added Pd/C (10%, 1.0 g). The reaction mixture was transferred to an autoclave and charged with hydrogen (50 psi). The mixture was stirred RT for 20 h and filtered. The filtrated was concentrated and the residue was purified on silica gel using a mixture of EtOAc and hexanes to give [(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-propyl]-(2,2-difluoro-ethyl)-carbamic acid tert-butylester (1.81 g, 93%). LRMS (M+Na+) m/z 391.2.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrated was concentrated
  3. customthe residue was purified on silica gel using
  4. additiona mixture of EtOAc and hexanes

Sources & evidence

ORD record
ord-7ed12fb6c4a74189ae0c24583661c9cf
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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