HCID 70567581, compound → (5Z,13E)-(8R,11R,12R,15S)-1-(N-Methylcarbamoyloxy)-11,15-dihydroxy-5,13-prostadien-9-one

HRID 237071Notes

Reaction equation

HRID 237071 reaction equation
[CH3:1][NH:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][C@@H:13]1[C@@H:17](/[CH:18]=[CH:19]/[C@@H:20]([O:26]C2CCCCO2)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:16]([O:33]C2CCCCO2)[CH2:15][C:14]1=[O:40])=[O:4]>C(O)(=O)C.O.O1CCCC1>[CH3:1][NH:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][C@@H:13]1[C@@H:17](/[CH:18]=[CH:19]/[C@@H:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:16]([OH:33])[CH2:15][C:14]1=[O:40])=[O:4]

Participants

3

Reactant 1

HCID 70567581HCID 70567581, compound

Product 1

HCID 70566919(5Z,13E)-(8R,11R,12R,15S)-1-(N-Methylcarbamoyloxy)-11,15-dihydroxy-5,13-prostadien-9-one

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

At 40°, 300 mg. of (5Z,13E)-(8R,11R,12R,15S)-1-(N-methylcarbamoyloxy)-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-9-one was agitated with 9 ml. of a mixture of glacial acetic acid/water/tetrahydrofuran (65/35/10) for 6 hours. The mixture was then evaporated to dryness under vacuum. After purifying the residue by chromatography on silica gel (ether/ethyl acetate 7+3), 145 mg. of the title compound was obtained as a colorless oil.

Workup

  1. customAt 40°
  2. customThe mixture was then evaporated to dryness under vacuum
  3. customAfter purifying the residue by chromatography on silica gel (ether/ethyl acetate 7+3), 145 mg

Sources & evidence

ORD record
ord-c14f7547fdb64b1bbd8c1ff53db3528a
Source dataset
uspto-grants-1979_06
Patent number
US04159343

Reaction notes

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