(R)-3-(Benzyloxy)-2-(2-((tert-butoxycarbonyl)amino)-2-methylpropanamido)propanoic acid → 2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-3-cyclohexylmethoxy-propionic acid

HRID 1036739Notes

Reaction equation

HRID 1036739 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:14][C:15](=[O:27])[C:16]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:18])[CH3:17])[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C)C.[Rh]>[C:23]([O:22][C:20]([NH:19][C:16]([CH3:18])([CH3:17])[C:15]([NH:14][CH:10]([CH2:9][O:8][CH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)[C:11]([OH:13])=[O:12])=[O:27])=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 1

HCID 10894202(R)-3-(Benzyloxy)-2-(2-((tert-butoxycarbonyl)amino)-2-methylpropanamido)propanoic acid2×

Product 1

HCID 710606792-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-3-cyclohexylmethoxy-propionic acid

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 5% rhodium on alumina (80 mg) and (R)-3-benzyloxy-2-(2-tert-butoxy carbonylamino-2-methyl-propionylamino)-propionic acid (500 mg, 1.31 mmol) (intermediate 3A) in isopropanol (12 ml) was stirred under a hydrogen atmosphere at room temperature overnight. To ensure completion, a further 120 mg of catalyst were added and the reaction was left to stir at room temperature under a hydrogen atmosphere for a further 5 h. The reaction mixture was filtered through Celite® (filter material) and concentrated in vacuo to give the title compound as a white solid.

Workup

  1. waitthe reaction was left
  2. stirringto stir at room temperature under a hydrogen atmosphere for a further 5 h
  3. filtrationThe reaction mixture was filtered through Celite® (filter material)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62795c4541d84828926bf91642557798
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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