Hydrochloric Acid → 9,21-Dihydroxypregn-4-ene-3,20-dione

HRID 1613975Notes

Reaction equation

HRID 1613975 reaction equation
Cl.C(N/[C:5](=[C:8]1/[CH2:9][CH2:10][C@@H:11]2[C@:25]/1([CH3:26])[CH2:24][CH2:23][C@@:22]1([OH:27])[C@H:12]2[CH2:13][CH:14]=[C:15]2[C@:20]1([CH3:21])[CH2:19][CH2:18][C:17]([O:28]C)=[CH:16]2)/[CH2:6][OH:7])=O.C[OH:31]>>[OH:27][C@:22]12[CH2:23][CH2:24][C@@:25]3([CH3:26])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C:5](=[O:31])[CH2:6][OH:7])[C@@H:12]1[CH2:13][CH2:14][C:15]1[C@:20]2([CH3:21])[CH2:19][CH2:18][C:17](=[O:28])[CH:16]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86746638(20Z)-20-Formamido-3-methoxypregna-3,5,17(20)-triene-9alpha,21-diol

Product 1

HCID 571918849,21-Dihydroxypregn-4-ene-3,20-dione

Procedure

Aqueous 5N hydrochloric acid (1 ml) was added to a stirred solution of (20Z)-20-formamido-3-methoxypregna-3,5,17(20)-triene-9α,21-diol (70 mg) in methanol (4 ml). The reaction mixture was stirred at room temperature for 1 hour, then extracted with ethyl acetate. The organic extract was washed with an aqueous sodium bicarbonate solution, twice with water, dried and concentrated under reduced pressure to afford the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with an aqueous sodium bicarbonate solution, twice with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dde6bdac6ce64edeb88aad39c90732a4
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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