N-[(2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3 hydroxypropionyl]-L-tryptophan benzyl ester → N-[(2RS,3RS)-3-cyclohexyl-3-hydroxy-2-(2-hydroxyphenylmethyl)propionyl]-L-tryptophan

HRID 1533280Notes

Reaction equation

HRID 1533280 reaction equation
C([O:8][C:9](=[O:48])[C@H:10]([CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[NH:41][CH:40]=1)[NH:11][C:12](=[O:37])[CH:13]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29]CC1C=CC=CC=1)[CH:14]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[OH:15])C1C=CC=CC=1>CO.[Pd]>[CH:16]1([CH:14]([OH:15])[CH:13]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[C:12]([NH:11][C@H:10]([C:9]([OH:48])=[O:8])[CH2:38][C:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[NH:41][CH:40]=2)=[O:37])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 1

HCID 70244716N-[(2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3 hydroxypropionyl]-L-tryptophan benzyl ester

Product 1

HCID 70247617N-[(2RS,3RS)-3-cyclohexyl-3-hydroxy-2-(2-hydroxyphenylmethyl)propionyl]-L-tryptophanYield 118.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[(2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionyl]-L-tryptophan benzyl ester (150 mg) in methanol (3 ml) was added 10% palladium on carbon (45 mg) and the mixture was stirred under hydrogen atmosphere for 3 hours. The mixture was filtered and the filtrate was evaporated under reduced pressure to give N-[(2RS,3RS)-3-cyclohexyl-3-hydroxy-2-(2-hydroxyphenylmethyl)propionyl]-L-tryptophan (128 mg).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-293f5a0406cd43db8ace6b94bf00a484
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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