Methanol → HCID 14695934, compound

HRID 1165452Notes

Reaction equation

HRID 1165452 reaction equation
[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:24])[CH2:9][CH2:10][C@@H:11]3[C@:21]4([CH2:22][OH:23])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].[C:25](OC(=O)C)(=[O:27])[CH3:26].CO>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:25]([O:23][CH2:22][C@@:21]12[C@@H:11]3[C@H:12]([C@H:7]4[C@:8]([CH3:24])([CH2:9][CH2:10]3)[C@@H:4]([C:2](=[O:3])[CH3:1])[CH2:5][CH2:6]4)[CH2:13][CH2:14][C:15]1=[CH:16][C:17](=[O:18])[CH2:19][CH2:20]2)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 15078219-Hydroxypregn-4-ene-3,20-dione

Product 1

HCID 14695934HCID 14695934, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 3.5 g of 19-hydroxyprogesterone and 0.25 g of 4-dimethylaminopyridine in 8 ml of pyridine is treated with 4 ml of acetic anhydride and stirred for 18 hours at room temperature. The solution is chilled to 0° C. and treated with 4 ml of methanol to consume excess acetic anhydride. After stirring for 15 minutes, the solution is concentrated to a small volume at reduced pressure and the residue is taken up in ether. The ether solution is washed three times with dilute hydrochloric acid, once with sodium bicarbonate solution and finally with brine. Drying and concentration gives 19-acetoxypregn-4-ene-3,20-dione which is obtained as a colorless solid upon crystallization from aqueous ethanol.

Workup

  1. temperatureThe solution is chilled to 0° C.
  2. customto consume excess acetic anhydride
  3. stirringAfter stirring for 15 minutes
  4. concentrationthe solution is concentrated to a small volume at reduced pressure
  5. washThe ether solution is washed three times with dilute hydrochloric acid
  6. customDrying
  7. concentrationconcentration

Sources & evidence

ORD record
ord-5d888baa7dc9492b8af68a49f5bced93
Source dataset
uspto-grants-1990_03
Patent number
US04910191

Reaction notes

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