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

HRID 434739Notes

Reaction equation

HRID 434739 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH2:4][CH2:5][CH2:6][CH2:7][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>[CH3:1][O:2][C:3](=[O:38])[CH2:4][CH2:5][CH2:6][CH2:7][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

4

Reactant 1

HCID 86738982(13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

Product 1

HCID 70595130(13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-dihydroxyprost-13-enoic acid methyl esterYield 73.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

By proceeding as described in Example 2 but using 435 mg of (13E)-(6RS,9α,11α,15S)-6,9-epoxy-11,15-bis-(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Example 5) dissolved in a mixture of 0.7 ml of tetrahydrofuran and 9 ml of 65% aqueous acetic acid, there were obtained 220 mg of the title compound having the following physical characteristics:

Sources & evidence

ORD record
ord-d3c4f13229ea44ab8b118804ba6bd725
Source dataset
uspto-grants-1983_08
Patent number
US04399147

Reaction notes

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