Pyridine → HCID 86733392, compound

HRID 1076053Notes

Reaction equation

HRID 1076053 reaction equation
[O:1]1[CH:15]2[CH:2]1[C:3](=[O:25])[C@@H:4]([C@H:14]2/[CH:16]=[CH:17]/[C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].N1C=CC=CC=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>O>[C:32]([O:24][C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])/[CH:17]=[CH:16]/[C@@H:14]1[C@@H:4]([CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[C:3](=[O:25])[CH:2]2[O:1][CH:15]12)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14427890HCID 14427890, compound

Product 1

HCID 86733392HCID 86733392, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

to a solution of 1 part of (5Z,13E,15S)-10ξ,11ξ-epoxy-15-hydroxy-9-oxoprosta-5,13-dien-1-oic acid in 30 parts of pyridine at 5° is added 10 parts of acetic anhydride. The resultant mixture is allowed to stand at 5° for 18 hours, whereupon it is poured into 10 volumes of water. The mixture thus obtained is allowed to stand for 1 hour, then extracted with ethyl acetate. The extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residual red oil is taken up in benzene; and the benzene solution is chromatographed on silica gel, using benzene and mixtures thereof with increasing amounts of ethyl acetate as developing solvents. From an eluate comprising 20% ethyl acetate in benzene, on evaporation of solvent, (5Z,13E,15S)-15-acetoxy-10ξ,11ξ-epoxy-9-oxoprosta-5,13-dien-1-oic acid is obtained as a pale yellow oil.

Workup

  1. customThe mixture thus obtained
  2. waitto stand for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationstripped of solvent by vacuum distillation
  7. customand the benzene solution is chromatographed on silica gel
  8. customFrom an eluate comprising 20% ethyl acetate in benzene, on evaporation of solvent

Sources & evidence

ORD record
ord-159ef1a4c1144fde866ced9a1daee21b
Source dataset
uspto-grants-1976_05
Patent number
US03954844

Reaction notes

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