HCID 53736563, compound → HCID 53918960, compound

HRID 977834Notes

Reaction equation

HRID 977834 reaction equation
[C:1]([O:15][C@H:16]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[C:28]([NH:36][C:37](=[O:53])[CH2:38][CH:39]2[C:52]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[O:46][C:45]3[C:40]2=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:27]=1)[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)(=[O:14])[CH2:2][CH2:3][C:4]([O:6]CC1C=CC=CC=1)=[O:5].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:15][C@H:16]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:33])([CH3:34])[CH3:35])=[C:28]([NH:36][C:37](=[O:53])[CH2:38][CH:39]2[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:45]=3[O:46][C:47]3[C:52]2=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:27]=1)[CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)(=[O:14])[CH2:2][CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 53736563HCID 53736563, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53918960HCID 53918960, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 337 mg (0.471 mmol) of (R)-1-(2-{4-t-butyl-3-[2-(9H-xanthen-9-yl)acetamido]phenyl}ethyl)-2-cyclohexylethyl benzyl succinate (prepared as described in Preparation 25) in 10 ml of ethyl acetate was vigorously stirred in a stream of hydrogen in the presence of 173 mg of 10% w/w palladium-on-charcoal. The reaction mixture was then filtered, and the catalyst was washed with ethyl acetate. The filtrate and the washings were combined, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through 15 g of silica gel, using a 1:19 by volume mixture of methanol and methylene chloride as the eluent, to give the title compound as a foam-like material.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washthe catalyst was washed with ethyl acetate
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe residue was purified by column chromatography through 15 g of silica gel
  5. additionby volume mixture of methanol and methylene chloride as the eluent

Sources & evidence

ORD record
ord-f1a9243b7bd449ea965abfb47d7f36cb
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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