beta-[[(1,1-Dimethylethoxy)carbonyl]amino]-alpha-hydroxybenzenebutanoic acid, 1-methylethyl ester → beta-[[(1,1-Dimethylethoxy)carbonyl]amino]-alpha-hydroxycyclohexanebutanoic acid, 1-methylethyl ester

HRID 846465Notes

Reaction equation

HRID 846465 reaction equation
[CH3:1][C:2]([CH3:24])([O:4][C:5]([NH:7][CH:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]([OH:16])[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[O:6])[CH3:3]>C(O)(C)C.[Rh]>[CH3:3][C:2]([CH3:1])([O:4][C:5]([NH:7][CH:8]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:9]([OH:16])[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[O:6])[CH3:24]

Participants

4

Reactant 1

HCID 21302835beta-[[(1,1-Dimethylethoxy)carbonyl]amino]-alpha-hydroxybenzenebutanoic acid, 1-methylethyl ester

Product 1

HCID 15674228beta-[[(1,1-Dimethylethoxy)carbonyl]amino]-alpha-hydroxycyclohexanebutanoic acid, 1-methylethyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 3776IsopropanolSolvent

Procedure

To β-[[(1,1-dimethylethoxy)carbonyl]amino]-α-hydroxybenzenebutanoic acid, 1-methylethyl ester (mixture of R-(R*,S*)] and [S-(R*,R*)]isomers) (Example E), 4.2 g (12.4 mmol), in isopropanol (100 ml) is added 10% rhodium on carbon, 1.0 g, and the mixture is stirred under a hydrogen atmosphere for 16 hours. The solution is filtered and evaporated in vacuo to give a 3.6 g (85%) of the title compound as a tan oil.

Workup

  1. filtrationThe solution is filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-43585fc029fb4ea59e106c38675c72fa
Source dataset
uspto-grants-1992_08
Patent number
US05135914

Reaction notes

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