HCID 69611306, compound → HCID 69611293, compound

HRID 1062330Notes

Reaction equation

HRID 1062330 reaction equation
C(OC([NH:11][C@@H:12]([CH2:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[C:30]([F:35])[CH:29]=1)[C@@H:13]([OH:26])[CH2:14][N:15]([CH2:24][CH3:25])[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:11][C@@H:12]([CH2:27][C:28]1[CH:29]=[C:30]([F:35])[CH:31]=[C:32]([F:34])[CH:33]=1)[C@@H:13]([OH:26])[CH2:14][N:15]([CH2:24][CH3:25])[NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18]

Participants

5

Reactant 2

HCID 69611306HCID 69611306, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69611293HCID 69611293, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of crude tert-butyl 2-((2S,3S)-3-{[(benzyloxy)carbonyl]-amino}-2-hydroxy-4-(3,5-difluorophenyl)butyl)-2-ethylhydrazinecarboxylate (906 mg, 1.8 mmol) in MeOH (15 mL) was added to 10% Pd/C (95 mg) and stirred in a hydrogen atmosphere (ambient pressure) for 4 h. The catalyst was filtered off over Celite and the filtrate was concentrated under reduced pressure to yield crude tert-butyl 2-((2S, 3S)-3-amino-2-hydroxy-4-(3,5difluorophenyl)butyl)-2-ethylhydrazinecarboxylate. MS (ESI+) for C17H27F2N3O3 m/z 360.2 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered off over Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5be4fcf78cdb40f8bd1d4fe1db33e73d
Source dataset
uspto-grants-2005_11
Patent number
US06960664B2

Reaction notes

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