Pyridine → HCID 22810209, compound

HRID 1701233Notes

Reaction equation

HRID 1701233 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[CH2:15][C@H:14]2[C@H:10]([CH2:11][C@@H:12]([OH:25])[C@@H:13]2/[CH:16]=[CH:17]/[C@@H:18]([OH:24])[CH2:19][CH2:20][C:21]#[C:22][CH3:23])[O:9]1)([OH:3])=O.[C:26]([O:29]C(=O)C)(=O)[CH3:27].[N:33]1C=CC=CC=1>CN(C)C1C=CN=CC=1.O>[C:26]([NH:33][C:1]([CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[CH2:15][C@H:14]2[C@H:10]([CH2:11][C@@H:12]([OH:25])[C@@H:13]2/[CH:16]=[CH:17]/[C@@H:18]([OH:24])[CH2:19][CH2:20][C:21]#[C:22][CH3:23])[O:9]1)=[O:3])(=[O:29])[CH3:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 22810216HCID 22810216, compound

Product 1

HCID 22810209HCID 22810209, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

400 mg. of (1S,5R,6R,7R,3R)-3-(4-carboxy-1-butyl)-7-hydroxy-6-[(E)-(3S)-3-hydroxy-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octane, 100 mg. of 4-dimethylaminopyridine, 0.5 ml. of acetic anhydride, and 1 ml. of pyridine are stirred for 16 hours at 20°, then combined with 0.2 ml. of water, agitated for another 2 hours, diluted with 50 ml. of water, and extracted repeatedly with methylene chloride. The extract is shaken in succession with dilute sulfuric acid and brine, dried over magnesium sulfate, and evaporated under vacuum. The dried residue (1 hour at 40° and 0.01 torr) is dissolved in 15 ml. of acetonitrile and, at 0°, a solution of 150 mg. of acetylisocyanate in 10 ml. of acetonitrile is added dropwise thereto. The mixture is stirred for another 2 hours at 20°, concentrated under vacuum, acidified with dilute sulfuric acid to pH 5, extracted repeatedly with ether, and the extract washed neutral with brine, dried over magnesium sulfate, and evaporated under vacuum.

Workup

  1. additiondiluted with 50 ml
  2. extractionof water, and extracted repeatedly with methylene chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum
  5. dissolutionThe dried residue (1 hour at 40° and 0.01 torr) is dissolved in 15 ml
  6. customat 0°
  7. additionof acetonitrile is added dropwise
  8. stirringThe mixture is stirred for another 2 hours at 20°
  9. concentrationconcentrated under vacuum
  10. extractionextracted repeatedly with ether
  11. washthe extract washed neutral with brine
  12. dry with materialdried over magnesium sulfate
  13. customevaporated under vacuum

Sources & evidence

ORD record
ord-7743b41ce0db45c5b81518c191e49ae8
Source dataset
uspto-grants-1980_03
Patent number
US04191694

Reaction notes

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