(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester → (13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid methyl ester

HRID 434732Notes

Reaction equation

HRID 434732 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH:7]([Br:38])[CH:8]1[O:37][C@H:11]2[CH2:12][C@@H:13]([O:30]C3CCCCO3)[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23]C3CCCCO3)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1>O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH:7]([Br:38])[CH:8]1[O:37][C@H:11]2[CH2:12][C@@H:13]([OH:30])[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1

Participants

5

Reactant 1

HCID 86737122(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

Product 1

HCID 86738979(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid methyl esterYield 80.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

360 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-Bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Example 1) were dissolved in a mixture of 0.7 ml of tetrahydrofuran and 7 ml of 65% aqueous acetic acid and the mixture was stirred at 40° to 45° C. for one hour. The reaction mixture was then diluted with ethyl acetate, washed with water and an aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:3) as eluent to give 210 mg of the title compound having the following physical characteristics:

Workup

  1. washwashed with water
  2. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of cyclohexane and ethyl acetate (1:3) as eluent

Sources & evidence

ORD record
ord-b612d572530f4d3496c0f589856f9868
Source dataset
uspto-grants-1983_08
Patent number
US04399147

Reaction notes

Loading…