HCID 69532806, compound → HCID 18188111, compound

HRID 1357869Notes

Reaction equation

HRID 1357869 reaction equation
C([O:8][CH2:9][CH2:10][CH:11]=[C:12]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:45])[CH2:27][C:28]2[CH:44]=[CH:43][C:31]3[N:32]=[C:33]([NH:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[CH3:42])[O:34][C:30]=3[CH:29]=2)=[CH:21][CH:20]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:8][CH2:9][CH2:10][CH2:11][CH:12]([C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:26](=[O:45])[CH2:27][C:28]2[CH:44]=[CH:43][C:31]3[N:32]=[C:33]([NH:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[CH3:42])[O:34][C:30]=3[CH:29]=2)=[CH:23][CH:24]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 69532806HCID 69532806, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18188111HCID 18188111, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 6-benzyloxy-3-{4-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-phenyl}-3-hexenoate (640 mg, Reference Example 22(a)) and 10% palladium on charcoal (250 mg) in ethanol (50 mL) was hydrogenated at room temperature and pressure. After 24 hours further catalyst (200 mg) was added and the mixture again subjected to a hydrogen atmosphere for a further 24 hours. The mixture was filtered through filter-aid and the filtrate evaporated to dryness to give the title compound (460 mg) as a colourless oil.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered
  3. filtrationthrough filter-aid
  4. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-2ada02c7813d444c9a0269d13fa2c732
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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