Acetic Anhydride → HCID 13322736, compound

HRID 1164155Notes

Reaction equation

HRID 1164155 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:26])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15]/[CH:16]=[CH:17]/[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:12](=[O:13])[CH2:11][C@H:10]1O.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH2:19][CH2:18]/[CH:17]=[CH:16]\[CH2:15][C@@H:14]1[C@@H:9](/[CH:8]=[CH:7]/[C@@H:6]([O:26][C:27](=[O:29])[CH3:28])[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH:10]=[CH:11][C:12]1=[O:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 643410731753-17-0

Product 1

HCID 13322736HCID 13322736, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 2.4 g of PGE2 methyl ester, 30 ml of acetic anhydride and 6 ml of pyridine was stirred at 35° C. for 40 hours. After concentration under reduced pressure, the residue was dissolved in diethyl ether, washed with water, and a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure to give 2.56 g of (5Z,13E)-(15S)-9-oxo-15-acetoxyprosta-5,10,13-trienoic acid methyl ester having the following physical characteristic:

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was dissolved in diethyl ether
  3. washwashed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5895f55388349619c5da916d5b4bdbb
Source dataset
uspto-grants-1983_01
Patent number
US04367237

Reaction notes

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