HCID 69242379, compound → HCID 69240381, compound

HRID 854674Notes

Reaction equation

HRID 854674 reaction equation
[CH3:1][C:2](=[CH2:35])[CH2:3][CH:4]([CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([O:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])[CH2:15]1)[C:5]([O:7]C(C)(C)C)=[O:6]>C(OCC)(=O)C.[Pd]>[CH3:1][CH:2]([CH3:35])[CH2:3][CH:4]([CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([O:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[O:25][C:26]=2[CH3:27])[CH2:15]1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 69242379HCID 69242379, compound

Product 1

HCID 69240381HCID 69240381, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

500 mg of tert-butyl 4-methyl-2-{2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]ethyl}pent-4-enoate are dissolved in 20 ml of ethyl acetate, and 50 mg of palladium (10% on activated carbon) are added. The mixture is stirred under an atmosphere of hydrogen (5 bar) for 5 hours. The catalyst is filtered off through Celite and the filtrate is concentrated under reduced pressure. The residue is dissolved in 20 ml of dichloromethane, and 10 ml of trifluoroacetic acid are added. The mixture is stirred at room temperature for 1 hour. 100 ml of toluene are added, and the solvents are then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 100 mg of 4-methyl-2-{2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]ethyl}pentanoic acid as an oil. C26H37NO4 (427.59), MS(ESI): 428 (M+H+).

Workup

  1. filtrationThe catalyst is filtered off through Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in 20 ml of dichloromethane
  4. addition10 ml of trifluoroacetic acid are added
  5. stirringThe mixture is stirred at room temperature for 1 hour
  6. addition100 ml of toluene are added
  7. customthe solvents are then removed under reduced pressure
  8. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-b9935c258e464f76b59120ee6651ca67
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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