Water → HCID 13190190, compound

HRID 1388650Notes

Reaction equation

HRID 1388650 reaction equation
C([O:4][CH2:5][C:6](=[O:31])[C@@:7]12[O:30][CH2:29][O:28][C@@H:8]1[CH2:9][C@@H:10]1[C@:24]2([CH3:25])[CH2:23][C@H:22]([OH:26])[C@H:21]2[C@H:11]1[CH2:12][CH2:13][C:14]1[C@:19]2([CH3:20])[CH:18]=[CH:17][C:16](=[O:27])[CH:15]=1)(=O)C.O.C(=O)([O-])[O-].[Ca+2]>CO>[OH:26][C@H:22]1[CH2:23][C@@:24]2([CH3:25])[C@@H:10]([CH2:9][C@H:8]3[O:28][CH2:29][O:30][C@:7]32[C:6](=[O:31])[CH2:5][OH:4])[C@H:11]2[C@H:21]1[C@:19]1([CH3:20])[C:14]([CH2:13][CH2:12]2)=[CH:15][C:16](=[O:27])[CH:17]=[CH:18]1

Participants

5

Reactant 3

HCID 962WaterHCID 10112Calcium CarbonateHCID 13190187HCID 13190187, compound

Product 1

HCID 13190190HCID 13190190, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.5 g of 21-acetoxy-11β-hydroxy-16α,17α-methylenedioxy-1,4-pregnadiene-3,20-dione is dissolved in 510 ml of methanol and 111 ml of water and refluxed under agitation with 1.5 g of calcium carbonate for 24 hours. The calcium carbonate is removed by vacuum-filtering; the filtrate is concentrated to turbidity and poured on water. After the usual working-up process, the crude product is purified on 115 g of silica gel with a methylene chloride-acetone gradient (0-20% acetone), thus isolating 758 mg of 11β,21-dihydroxy-16α,17α-methylenedioxy-1,4-pregnadiene-3,20-dione, mp 220°-223° C. (decomposition).

Workup

  1. customThe calcium carbonate is removed
  2. filtrationby vacuum-filtering
  3. concentrationthe filtrate is concentrated to turbidity
  4. additionpoured on water
  5. customthe crude product is purified on 115 g of silica gel with a methylene chloride-acetone gradient (0-20% acetone)

Sources & evidence

ORD record
ord-570083fb7ca345a29b306214a0a2ce9d
Source dataset
uspto-grants-1984_02
Patent number
US04432976

Reaction notes

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