HCID 86625864, compound → HCID 86625865, compound

HRID 1692190Notes

Reaction equation

HRID 1692190 reaction equation
[C:1]1([CH3:32])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C@@H:12]([O:22][CH2:23][P:24]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])=[O:25])[CH2:13][O:14]CC2C=CC=CC=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1>[Pd].CO>[C:1]1([CH3:32])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C@@H:12]([O:22][CH2:23][P:24]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:27])[CH3:28])=[O:25])[CH2:13][OH:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 86625864HCID 86625864, compound

Product 1

HCID 86625865HCID 86625865, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (1.05 g) was added to a solution of 7 (11.5 g, 22.4 mmol) in methanol (150 ml) and the mixture was hydrogenated at room temperature under atmospheric pressure for 24 h. The solid was filtered off through Celite, washed with methanol (2×100 ml) and combined filtrates were concentrated in vacuo. The syrupy residue was chromatographed on a column of silica gel (400 ml) in ethyl acetate. Product containing fractions were evaporated to give 7.7 g (81%) of compound 8 as a colorless syrup,

Workup

  1. filtrationThe solid was filtered off through Celite
  2. washwashed with methanol (2×100 ml)
  3. concentrationwere concentrated in vacuo
  4. customThe syrupy residue was chromatographed on a column of silica gel (400 ml) in ethyl acetate
  5. additionProduct containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-0e599832e77c4857a04edff4fec04b1f
Source dataset
uspto-grants-2012_04
Patent number
US08153787B2

Reaction notes

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