N-(tert-Butoxycarbonyl)-N-phenylglycine → n-Boc-n-cyclohexylglycine

HRID 1061674Notes

Reaction equation

HRID 1061674 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Rh]>[C:1]([O:5][C:6]([N:8]([CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 21905636N-(tert-Butoxycarbonyl)-N-phenylglycineHCID 178418361HCID 178418361, compound

Product 1

HCID 10563100n-Boc-n-cyclohexylglycine

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, 5% rhodium/alumina (3.00 g) is added to a solution of DL-N-tert-butoxycarbonylphenylglycine in ethanol (80 ml). The atmosphere is replaced with pressurized hydrogen (4.0 kgf/cm2) and stirred for ten days. The 5% rhodium/alumina is filtered out. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography to give the titled reference compound (25.0 g).

Workup

  1. filtrationThe 5% rhodium/alumina is filtered out
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e6f0bace87a84e8fb9251569ca7771d2
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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