Acetic Acid → HCID 86733285, compound

HRID 1606343Notes

Reaction equation

HRID 1606343 reaction equation
Br[CH2:2][C:3](=[O:27])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:26])[C@@H:14]([O:24][CH3:25])[CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[C:28]([OH:31])(=[O:30])[CH3:29].C(N(CC)CC)C>CC(C)=O.C(Cl)(Cl)Cl>[C:28]([O:31][CH2:2][C:3](=[O:27])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:26])[C@@H:14]([O:24][CH3:25])[CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1)(=[O:30])[CH3:29]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 86733284HCID 86733284, compound

Product 1

HCID 86733285HCID 86733285, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

21-Bromo-3α-hydroxy-2β-methoxy-5α-pregnane-11,20-dione (600 mg.) was dissolved in dry acetone (15 ml.) and added to a mixture of glacial acetic acid (2 ml.) and triethylamine (3ml.) and refluxed for 41/2 hours. The mixture was diluted with chloroform, washed with water, dried and evaporated to a foam. Purification by preparative tlc followed by crystallisation from ethyl acetate and petrol gave the title compound (230 mg.) as colourless plates; m.p. 177°-180° [α]D + 112°.

Workup

  1. temperaturerefluxed for 41/2 hours
  2. washwashed with water
  3. customdried
  4. customevaporated to a foam
  5. customPurification by preparative tlc
  6. customfollowed by crystallisation from ethyl acetate and petrol

Sources & evidence

ORD record
ord-285abf0a83004e4ead3b87d05ca6dd01
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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