(13E)-(6RS,9alpha,11alpha,15S)-6,9-epithio-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid 1,3-bisstearoyloxy-2-propyl ester → (13E)-(6RS,9alpha,11alpha,15S)-6,9-Epithio-11,15-dihydroxyprost-13-enoic acid 1,3-bisstearoyloxy-2-propyl ester

HRID 1164161Notes

Reaction equation

HRID 1164161 reaction equation
[C:1]([O:20][CH2:21][CH:22]([O:44][C:45](=[O:80])[CH2:46][CH2:47][CH2:48][CH2:49][CH:50]1[S:79][C@H:53]2[CH2:54][C@@H:55]([O:72]C3CCCCO3)[C@H:56](/[CH:57]=[CH:58]/[C@@H:59]([O:65]C3CCCCO3)[CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[C@H:52]2[CH2:51]1)[CH2:23][O:24][C:25](=[O:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CO>[C:1]([O:20][CH2:21][CH:22]([O:44][C:45](=[O:80])[CH2:46][CH2:47][CH2:48][CH2:49][CH:50]1[S:79][C@H:53]2[CH2:54][C@@H:55]([OH:72])[C@H:56](/[CH:57]=[CH:58]/[C@@H:59]([OH:65])[CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[C@H:52]2[CH2:51]1)[CH2:23][O:24][C:25](=[O:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 1

HCID 86738739(13E)-(6RS,9alpha,11alpha,15S)-6,9-epithio-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid 1,3-bisstearoyloxy-2-propyl ester

Product 1

HCID 86738738(13E)-(6RS,9alpha,11alpha,15S)-6,9-Epithio-11,15-dihydroxyprost-13-enoic acid 1,3-bisstearoyloxy-2-propyl esterYield 66.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Under an atmosphere of nitrogen, a mixture of 51 mg of (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15-bis-(tetrahydropyran-2-yloxy)prost-13-enoic acid 1,3-bisstearoyloxy-2-propyl ester, 2.5 mg of p-toluenesulphonic acid-pyridine complex and 2 ml of methanol was stirred at 50° C. for 1.5 hours, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 29 mg of the title compound having the following physical characteristics:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel using
  3. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-ba219fde375644f7b9d3623ef518e123
Source dataset
uspto-grants-1983_01
Patent number
US04367237

Reaction notes

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