HCID 70589641, compound → HCID 70589718, compound

HRID 225386Notes

Reaction equation

HRID 225386 reaction equation
[C:1]([NH:4][C:5](=[O:42])[CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@@H:12]1[C@@H:16](/[CH:17]=[CH:18]/[C@@H:19]([O:27]C2CCCCO2)[C:20]([CH3:26])([CH3:25])[CH2:21][C:22]#[C:23][CH3:24])[C@H:15]([O:34]C2CCCCO2)[CH2:14][C:13]1=[O:41])(=[O:3])[CH3:2]>C(O)(=O)C.O.C1COCC1>[C:1]([NH:4][C:5](=[O:42])[CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@@H:12]1[C@@H:16](/[CH:17]=[CH:18]/[C@@H:19]([OH:27])[C:20]([CH3:25])([CH3:26])[CH2:21][C:22]#[C:23][CH3:24])[C@H:15]([OH:34])[CH2:14][C:13]1=[O:41])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 70589641HCID 70589641, compound

Product 1

HCID 70589718HCID 70589718, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

400 mg. of (5Z,13E)-(11R,15R)-16,16-dimethyl-9-oxo-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid acetylamide is agitated for 16 hours at 25° with 12 ml. of a mixture of glacial acetic acid/water/THF (65/35/10), evaporated under vacuum, and the residue purified by column chromatography on silica gel. With methylene chloride/2-5% methanol, 190 mg. of the title compound is obtained as an oil.

Workup

  1. customevaporated under vacuum
  2. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5cddab676ff54393a42b848ed00f3e8b
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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