HCID 69611256, compound → HCID 69611254, compound

HRID 1062327Notes

Reaction equation

HRID 1062327 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 69611256HCID 69611256, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69611254HCID 69611254, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 2-((2R,3S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutyl)-2-ethylhydrazinecarboxylate (3.11 g, 6.8 mmol) in methanol (50 mL) was added to 10% Pd/C (0.32 g) and stirred in a hydrogen atmosphere (@ ambient pressure) for 5 h. The reaction was filtered through Celite and the filtrate concentrated under reduced pressure to yield tert-butyl 2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-2-ethylhydrazinecarboxylate (2.2 g) as an oil. MS (ESI+) for C17H29N3O3 m/z 324.3 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-6f4bca79ffc745628693f7e8ca441620
Source dataset
uspto-grants-2005_11
Patent number
US06960664B2

Reaction notes

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