Acetic Acid → HCID 86736875, compound

HRID 1701452Notes

Reaction equation

HRID 1701452 reaction equation
[Cl:1][CH2:2][C:3]([O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[C@H:16]2[C@H:7]1[C@:8]1([CH3:28])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][C@@H:11]2[O:27][C@@H:10]2[CH2:9]1)=[O:4].C(=O)(O)[O-].[Na+].[C:34]([OH:37])(=[O:36])[CH3:35]>>[C:34]([O:37][C@H:10]1[CH2:9][C@@:8]2([CH3:28])[C@@H:13]([CH2:14][CH2:15][C@@H:16]3[C@@H:7]2[C@@H:6]([O:5][C:3](=[O:4])[CH2:2][Cl:1])[CH2:25][C@@:24]2([CH3:26])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[CH2:12][C@@H:11]1[OH:27])(=[O:36])[CH3:35]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 86736871HCID 86736871, compound

Product 1

HCID 86736875HCID 86736875, compound

Procedure

11β-Chloroacetoxy-2α,3α-epoxy-5α-pregnan-20-one (5 g) was dissolved in glacial acetic acid (25 ml) and heated on a steam bath for 3.1/2 hrs. The solution was poured into saturated sodium bicarbonate solution, the white precipitate filtered off, washed well with water and dried. Preparation thick layer chromatography in ethyl acetate-petrol gave the title compound as a white foam (3.26 g). [α]D +93.2°.

Workup

  1. temperatureheated on a steam bath for 3
  2. custom1/2 hrs
  3. filtrationthe white precipitate filtered off
  4. washwashed well with water
  5. customdried
  6. customPreparation thick layer chromatography in ethyl acetate-petrol

Sources & evidence

ORD record
ord-07d3933ddb2648a9b35ff75fbf0b1fd1
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

Loading…