Hydrochloric Acid → HCID 22789223, compound

HRID 1606474Notes

Reaction equation

HRID 1606474 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@:21]42[O:26][C@H:20]4[CH2:19][C@@:18]2([CH3:27])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].[ClH:28].C(=O)(O)[O-].[Na+]>CCOCC>[C:1]([O:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@:21]2([Cl:28])[C@@H:20]([OH:26])[CH2:19][C@@:18]2([CH3:27])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86733323HCID 86733323, compound

Product 1

HCID 22789223HCID 22789223, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3α-Acetoxy-9β,11β-epoxy-5α-pregnan-20-one (500 mg.) was dissolved in ether and the ether evaporated to leave a gummy residue. Hydrochloric acid (11.6N; 5ml.) was added and the reaction stirred for 4 min., it was then poured into aqueous sodium bicarbonate solution and the solid filtered off, washed with water and dried. Crystallisation from methyl acetate-petrol gave the title compound (250 mg.), m.p. 175°-179°. Recrystallisation from aqueous acetone gave a sample m.p. 177°-179°, [α]D + 97°.

Workup

  1. customthe ether evaporated
  2. customto leave a gummy residue
  3. filtrationthe solid filtered off
  4. washwashed with water
  5. customdried
  6. customCrystallisation from methyl acetate-petrol

Sources & evidence

ORD record
ord-495a5927e7984241b3f429e69948b6a4
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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