HCID 69611259, compound → HCID 69611275, compound

HRID 1062328Notes

Reaction equation

HRID 1062328 reaction equation
C(OC([NH:11][C@@H:12]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][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]=[CH:30][CH:31]=[CH:32][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 69611259HCID 69611259, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69611275HCID 69611275, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of crude tert-butyl 2-((2S,3S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutyl)-2-ethylhydrazinecarboxylate (502 mg, 1.1 mmol) in MeOH (10 mL) was added to 10% Pd/C (5.2 mg) and stirred in a hydrogen atmosphere (@ ambient pressure) for 6 h. The reaction was filtered through Celite and the filtrate concentrated under reduced pressure to yield crude tert-butyl 2-((25,3S)-3-amino-2-hydroxy-4-phenylbutyl)-2-ethylhydrazinecarboxylate (293 mg). MS (ESI+) for C17H29N3O3 m/z 324.2 (M+H)+.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-17e2cf28904945a396e165f2e779b962
Source dataset
uspto-grants-2005_11
Patent number
US06960664B2

Reaction notes

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