HCID 68427289, compound → HCID 68428712, compound

HRID 2191271Notes

Reaction equation

HRID 2191271 reaction equation
C([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([O:19][CH:20]([CH:22]3[CH2:24][CH2:23]3)[CH3:21])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[CH:22]1([CH:20]([O:19][C:17]2[CH:16]=[CH:15][C:13]3[CH2:14][NH:8][CH2:9][CH2:10][O:11][C:12]=3[N:18]=2)[CH3:21])[CH2:24][CH2:23]1

Participants

4

Reactant 1

HCID 68427289HCID 68427289, compound

Product 1

HCID 68428712HCID 68428712, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the compound obtained in step 1 (0.15 g), 20% Pd(OH)2/C (0.020 g) and methanol (3 mL) was stirred at 50° C. for 15 hr under a hydrogen atmosphere. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane) to give the title compound (0.11 g, quantitatively) as a colorless oil.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-17cce505a31d484c9ac8dce2a08b15c7
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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