HCID 135665581, compound → HCID 135665580, compound

HRID 1988259Notes

Reaction equation

HRID 1988259 reaction equation
C(OC([CH2:11][NH:12][CH:13]([CH:38]([CH3:40])[CH3:39])[C:14]([NH:16][CH:17]([C:30]1[NH:35][C:34](=[O:36])[CH:33]=[C:32]([CH3:37])[N:31]=1)[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=1)=[O:15])=O)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].CO>[C:26]([C:21]1[CH:20]=[C:19]([CH2:18][CH:17]([C:30]2[NH:35][C:34](=[O:36])[CH:33]=[C:32]([CH3:37])[N:31]=2)[NH:16][C:14](=[O:15])[CH:13]([NH:12][CH3:11])[CH:38]([CH3:40])[CH3:39])[CH:24]=[CH:23][C:22]=1[OH:25])([CH3:27])([CH3:28])[CH3:29]

Participants

5

Reactant 2

HCID 135665581HCID 135665581, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135665580HCID 135665580, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(1-(2-(benzyloxycarbonylmethylamino)-3-methyl-butyrylamino)-2-(3-tert-butyl-4-hydroxyphenyl)ethyl)-6-methyl-4-pyrimidinone (0.71 g, 1.294 mmol), 20% palladium hydroxide/carbon (0.15 g) and methanol (20 ml) was stirred in a hydrogen atmosphere for 4 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: methylene chloride:methanol=15:1), giving two diastereoisomers A and B of the titled compound, A (296 mg, 38%) being eluted first and then B (77 mg, 9.4%). (A)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d178835bc2a948458ec3534d3eed6966
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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