HCID 54146870, compound → HCID 54518313, compound

HRID 843148Notes

Reaction equation

HRID 843148 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[O:12][C:13]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][CH2:24][N:25](C(OCC4C=CC=CC=4)=O)[C:26]([CH3:29])([CH3:28])[CH3:27])[C:14]=3[C:15]=2[CH3:16])[O:9][CH:10]=1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[O:12][C:13]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:14]=3[C:15]=2[CH3:16])[O:9][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 54146870HCID 54146870, compound

Product 1

HCID 54518313HCID 54518313, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-{4-[3-(Benzyloxycarbonyl-tert-butyl-amino)-propoxy]-3-methyl-benzofuran-2-yl}-oxazole-4-carboxylic acid ethyl ester (20 mg) in methanol (5 ml) was treated with catalytic amount of 10% palladium on carbon under hydrogen atmosphere at room temperature for 18 hours. After filtration, evaporation and purification by silica gel column chromatography using 10:1 mixture of dichloromethane and methanol as an eluent, 2-{4-[3-(tert-butylamino)-propoxy]-3-methyl-benzofuran-2-yl}-oxazole-4-carboxylic acid ethyl ester was obtained as a white solid (8 mg). FAB-MS: m/z 401.

Workup

  1. filtrationAfter filtration, evaporation and purification by silica gel column chromatography
  2. addition10:1 mixture of dichloromethane and methanol as an eluent

Sources & evidence

ORD record
ord-ae444b8690fa4fd4869251ac388b3634
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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