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

HRID 1007750Notes

Reaction equation

HRID 1007750 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-e87ee7afbe1a4db3b857d63794c6ae14
Source dataset
uspto-grants-2004_09
Patent number
US06797700B2

Reaction notes

Loading…