HCID 86594509, compound → HCID 58763411, compound

HRID 858204Notes

Reaction equation

HRID 858204 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH2:22][CH:23]=[C:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])[CH2:17]1>C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH2:22][CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])[CH2:17]1

Participants

3

Reactant 1

HCID 86594509HCID 86594509, compound

Product 1

HCID 58763411HCID 58763411, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

81 mg of 5-{2-[cis-3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyl]-ethylidene}thiazolidine-2,4-dione are dissolved in 10 ml of ethyl acetate, and 10 mg of paladium (10% on activated carbon) are added. The mixture is stirred under an atmosphere of hydrogen (5 bar) for 9 hours. The catalyst is then filtered off through Celite and the filtrate is concentrated under reduced pressure. The residue is purified by RP-HPLC. This gives 60 mg of 5-{2-[cis-3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyl]-ethyl}thiazolidine-2,4-dione as a lyophilisate.

Workup

  1. addition10 mg of paladium (10% on activated carbon) are added
  2. filtrationThe catalyst is then filtered off through Celite
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-c7871101973c460482d9d43914bde3ab
Source dataset
uspto-grants-2006_12
Patent number
US07148246B2

Reaction notes

Loading…