Acetic Acid → Methyl α-[[(1,1-dimethylethoxy)carbonyl]amino]cyclohexaneacetate

HRID 650662Notes

Reaction equation

HRID 650662 reaction equation
[C:1]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(O)(=O)C.[H][H]>CO.[Rh]>[C:1]([NH:8][CH:9]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14427180HCID 14427180, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13773588Methyl α-[[(1,1-dimethylethoxy)carbonyl]amino]cyclohexaneacetate

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

N-BOC-a-phenylglycine, methyl ester (1.2 g) is dissolved in methanol (50 ml) containing acetic acid (1 ml). 5% rhodium on aluminum powder (0.60 g) is added and the mixture shaken under 50 psi hydrogen for about 18 hours. The mixture is filtered, evaporated in vacuo , and the residue taken up into ethyl acetate. The organic solution is washed with water, saturated sodium bicarbonate solution, water, brine, dried over magnesium sulfate, filtered, evaporated in vacuo to give N-BOC-a-cyclohexylglycine, methyl ester.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated in vacuo
  3. washThe organic solution is washed with water, saturated sodium bicarbonate solution, water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ec6fc8a8b41c4807ab9ef5604f78df96
Source dataset
uspto-grants-2001_08
Patent number
US06274705B1

Reaction notes

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