HCID 70589546, compound → HCID 70589853, compound

HRID 225385Notes

Reaction equation

HRID 225385 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[CH3:6][C:7]([CH3:44])([CH2:40][C:41]#[C:42][CH3:43])[C@H:8]([O:33]C1CCCCO1)/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:15]([CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:14](=[O:25])[CH2:13][C@H:12]1[O:26]C1CCCCO1>C(O)(=O)C.O.C1COCC1>[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[CH3:6][C:7]([CH3:44])([CH2:40][C:41]#[C:42][CH3:43])[C@H:8]([OH:33])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:15]([CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:14](=[O:25])[CH2:13][C@H:12]1[OH:26]

Participants

3

Reactant 1

HCID 70589546HCID 70589546, compound

Product 1

HCID 70589853HCID 70589853, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

At 25°, 400 mg. of (5Z,13E)-(11R,15R)-16,16-dimethyl-9-oxo-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid methylsulfonamide is agitated for 16 hours with 12 ml. of a mixture of glacial acetic acid/water/THF (65/35/10). The mixture is evaporated under vacuum and the residue purified by column chromatography on silica gel. With methylene chloride/2-5% methanol 202 mg. of the title compound is obtained in the form of an oil.

Workup

  1. customAt 25°
  2. customThe mixture is evaporated under vacuum
  3. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8df87cf06d3943ab8fda1d792e9e43d2
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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