Acetic Anhydride → HCID 15580497, compound

HRID 2285927Notes

Reaction equation

HRID 2285927 reaction equation
[OH:1][C@@H:2]([C:21]([CH3:27])([CH3:26])[CH2:22][CH2:23][CH2:24][CH3:25])/[CH:3]=[CH:4]/[C@H:5]1[C@@H:9]([CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7][C@H:6]1[CH3:20].[C:28](OC(=O)C)(=[O:30])[CH3:29]>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[C:28]([O:1][C@@H:2]([C:21]([CH3:26])([CH3:27])[CH2:22][CH2:23][CH2:24][CH3:25])/[CH:3]=[CH:4]/[C@H:5]1[C@@H:9]([CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7][C@H:6]1[CH3:20])(=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 12795615HCID 12795615, compound

Product 1

HCID 15580497HCID 15580497, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 156 mg of (8R,11R,12S,15R,5Z,13E)-15-hydroxy-11,16,16-trimethyl-9-oxoprosta-5,13-dien-1-oic acid, 100 mg of acetic, anhydride, 21 mg of 4-(dimethylamino)pyridine, and 2 ml of triethylamine was stirred at room temperature under a positive nitrogen atmosphere. After 16 hr, the reaction mixture was partitioned between ethyl acetate-water and the organic layer separated, dried (MgSO4), and condensed by rotary evaporation. The residual material was purified by chromatography over Sephadex LH-20 (hydroxypropylated beaded dextran) using chloroform/hexane (3:2) as the eluant to yield 112 mg (65%) of (8R,11R,12S,15R,5Z,13E)-15-acetyloxy-11,16,16-trimethyl-9-oxoprosta-5,13-dien-1-oic acid. [α]D25 -78.52 (CHCl3, c 1.02).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate-water
  2. customthe organic layer separated
  3. customdried
  4. custom(MgSO4), and condensed
  5. customby rotary evaporation
  6. customThe residual material was purified by chromatography over Sephadex

Sources & evidence

ORD record
ord-56ffed13f72143229aa73585ea6ce015
Source dataset
uspto-grants-1982_04
Patent number
US04325970

Reaction notes

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