HCID 46862983, compound → Amitiza

HRID 1049957Notes

Reaction equation

HRID 1049957 reaction equation
[F:1][C:2]([F:34])([CH2:30][CH2:31][CH2:32][CH3:33])[C:3](=[O:29])/[CH:4]=[CH:5]/[C@H:6]1[C@H:10]([O:11]CC2C=CC=CC=2)[CH2:9][C:8](=[O:19])[C@@H:7]1[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27]>C(OCC)(=O)C.[Pd]>[CH3:33][CH2:32][CH2:31][CH2:30][C:2]([F:34])([F:1])[C@:3]1([OH:29])[O:11][C@@H:10]2[CH2:9][C:8]([C@H:7]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C@H:6]2[CH2:5][CH2:4]1)=[O:19]

Participants

4

Reactant 1

HCID 46862983HCID 46862983, compound

Product 1

HCID 157920AmitizaYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (Z)-7-[(1R,2R,3R)-2-((E)-4,4-difluoro-3-oxo-1-octenyl)-3-(phenylmethoxy)-5-oxocyclopentyl]-5-heptenoic acid (10, R1 is phenyl, R2 and R3 are H, R6 is H, and the S/D bond between the carbon at position 9b1 and the carbon at position 9b2 is a double bond, 50 mg) in ethyl acetate (5 mL), was added 10% palladium on carbon (5 mg) and the suspension was hydrogenated at atmospheric pressure for 10 hours. After the completion of the reaction, the mixture was filtered through Celite® and the crude material was re-crystallized using ethyl acetate/heptanes to yield Lubiprostone as a crystalline material in 70% yield.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe mixture was filtered through Celite®
  3. customthe crude material was re-crystallized

Sources & evidence

ORD record
ord-6003dcafa5c246e0a38415e0f880b97d
Source dataset
uspto-grants-2016_07
Patent number
US09382272B2

Reaction notes

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