Water → HCID 86734292, compound

HRID 1973725Notes

Reaction equation

HRID 1973725 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7](=[O:29])[C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C:23](=[O:27])[CH2:24]2)[C@:20]2([CH3:21])[C@H:15]([CH2:16][C@H:17]([OH:28])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)=[O:5])C.C(=O)(O)[O-].[K+].O>CO>[OH:28][C@@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@@H:15]([CH2:14][CH2:13][C@@H:12]3[C@@H:22]2[C:23](=[O:27])[CH2:24][C@@:25]2([CH3:26])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[C:7](=[O:29])[CH2:6][C:4]([O:3][CH3:1])=[O:5])[CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 516893Potassium BicarbonateHCID 86734293HCID 86734293, compound

Product 1

HCID 86734292HCID 86734292, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 21-ethoxycarbonyl-3α-hydroxy-5α-pregnane-11,20-dione 850 mg) in dry methyl alcohol (40 ml) was treated with potassium bicarbonate (1.02 g) and the mixture was refluxed, under nitrogen, for 1 hr., then poured into water. The product was extracted with ethyl acetate, and the extract washed with water, dried, and evaporated. The residue (506 mg) was purified by preparative t.l.c. and crystallisation from methyl acetate/petrol gave title compound (157 mg) m.p. 150°-152°, [α]D + 111.2°, λmax. 248.5 nm (ε 4,185).

Workup

  1. temperaturethe mixture was refluxed, under nitrogen, for 1 hr
  2. extractionThe product was extracted with ethyl acetate
  3. washthe extract washed with water
  4. customdried
  5. customevaporated
  6. customThe residue (506 mg) was purified by preparative t.l.c
  7. customand crystallisation from methyl acetate/petrol

Sources & evidence

ORD record
ord-c16b6b3845814bd59584c2930fd0ec4f
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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