Methanol → (13E)-(6RS,9alpha,11alpha,15S)-6,9-Epithio-11,15-dihydroxyprost-13-enoic acid decyl ester

HRID 1164157Notes

Reaction equation

HRID 1164157 reaction equation
[N+](=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[N-].[S:13]1[C@H:24]2[CH2:25][C@@H:26]([OH:37])[C@H:27](/[CH:28]=[CH:29]/[C@@H:30]([OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C@H:23]2[CH2:22][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].CO>C(Cl)Cl>[CH2:3]([O:21][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[S:13][C@H:24]2[CH2:25][C@@H:26]([OH:37])[C@H:27](/[CH:28]=[CH:29]/[C@@H:30]([OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C@H:23]2[CH2:22]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 15635947DiazodecaneHCID 86738733(13E)-(6RS,9alpha,11alpha,15S)-6,9-epithio-11,15-dihydroxyprost-13-enoic acid

Product 1

HCID 86738734(13E)-(6RS,9alpha,11alpha,15S)-6,9-Epithio-11,15-dihydroxyprost-13-enoic acid decyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ethereal solution of diazodecane was added dropwise to a solution of 100 mg of (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15-dihydroxyprost-13-enoic acid (prepared as described in Example 2) in 5 ml of methylene chloride at room temperature with stirring until the starting material was not detected by thin layer chromatography on silica gel using a 2% v/v solution of methanol in ethyl acetate as developing solvent. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:1) as eluent to give 109 mg of the title compound having the following physical characteristics:

Workup

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

Sources & evidence

ORD record
ord-d137306047c94a5ba922b0939d878a9a
Source dataset
uspto-grants-1983_01
Patent number
US04367237

Reaction notes

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