(alphaR,betaR)-N-benzyloxycarbonyl-5-chloro-1-ethyl-beta-methyltryptophan methyl ester → (alphaR,betaR)-5-chloro-1-ethyl-beta-methyltryptophan methyl ester

HRID 1382252Notes

Reaction equation

HRID 1382252 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C@@H:4]([C@H:16]([CH3:29])[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=2)[N:19]([CH2:27][CH3:28])[CH:18]=1)[NH:5]C(OCC1C=CC=CC=1)=O>CO>[CH3:1][O:2][C:3](=[O:30])[C@@H:4]([C@H:16]([CH3:29])[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=2)[N:19]([CH2:27][CH3:28])[CH:18]=1)[NH2:5]

Participants

3

Reactant 1

HCID 14152055(alphaR,betaR)-N-benzyloxycarbonyl-5-chloro-1-ethyl-beta-methyltryptophan methyl ester

Product 1

HCID 14152057(alphaR,betaR)-5-chloro-1-ethyl-beta-methyltryptophan methyl esterYield 85.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (αR,βR)-Nα -Benzyloxycarbonyl-5-chloro-1-ethyl-β-methyltryptophan methyl ester (4.17 g) in methanol (100 ml) containing 10% paradium on charcoal (0.5 g) was hydrogenated. After removal of the catalyst and evaporation of the solvent, (αR,βR)-5-chloro-1-ethyl-β-methyltryptophan methyl ester (2.45 g) was obtained as a yellow amorphous powder.

Workup

  1. customAfter removal of the catalyst and evaporation of the solvent

Sources & evidence

ORD record
ord-aa2f9d0ed93b4ba8bfba10d4eb0a218b
Source dataset
uspto-grants-1989_02
Patent number
US04806538

Reaction notes

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