Acetic Anhydride → HCID 86750053, compound

HRID 1080640Notes

Reaction equation

HRID 1080640 reaction equation
[OH:1][C@H:2]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@:8]3([OH:27])[CH2:9][CH2:10][C@@H:11]2/[CH:12]=[CH:13]/[C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:28]([O:1][C@H:2]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@:8]3([OH:27])[CH2:9][CH2:10][C@@H:11]2/[CH:12]=[CH:13]/[C:14]([O:16][CH3:17])=[O:15])[CH2:3]1)(=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 70682437methyl (E)-3beta,14beta-dihydroxy-5beta-pregn-20-ene-21-carboxylate

Product 1

HCID 86750053HCID 86750053, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 9.00 g of methyl (E)-3β,14β-dihydroxy-5β-pregn-20-ene-21-carboxylate (Boutagy J. and Thomas R., Aust. J. Pharm. Sci., 1972, NS1, 67) in 40 ml of pyridine, 0.04 g of 4-dimethylaminopyridine and 11.5 ml of acetic anhydride were added at room temperature, under nitrogen atmosphere. After 4 hrs the reaction was concentrated under reduced pressure, neutralized with aqueous sodium dihydrogenphosphate and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness to give 9.05 g of methyl (E)-3β-acetoxy-14β-hydroxy-5β-pregn-20-ene-21-carboxylate.

Workup

  1. concentrationAfter 4 hrs the reaction was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-9fb455343351469e85bc1b730572e210
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

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