Hydrochloric Acid → (20R)-11beta,17,20-trihydroxy-3-oxo-1,4-pregnadien-21-oic acid

HRID 1589963

Reaction equation

HRID 1589963 reaction equation
[OH:1][C@H:2]1[CH2:24][C@@:23]2([CH3:25])[C@@H:13]([CH2:14][CH2:15][C@:16]2([OH:26])[C@@H:17]([OH:22])[C:18]([O:20]C)=[O:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:28])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:27])[CH:6]=[CH:5]1.[OH-].[Na+].Cl.O>CO>[OH:1][C@H:2]1[CH2:24][C@@:23]2([CH3:25])[C@@H:13]([CH2:14][CH2:15][C@:16]2([OH:26])[C@@H:17]([OH:22])[C:18]([OH:20])=[O:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:28])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:27])[CH:6]=[CH:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178942Methyl (11beta,20R)-11,17,20-trihydroxy-3-oxopregna-1,4-dien-21-oate2×

Product 1

HCID 13313067(20R)-11beta,17,20-trihydroxy-3-oxo-1,4-pregnadien-21-oic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Example 9 (Product 9A), 500 mg, in methanol (50 ml), 1N NaOH (1 ml) was added. After 20 min in ice bath, the mixture was neutrlized with 0.1N HCl and 300 ml of distilled water was added. After extracting with ethyl acetate (300 ml), the organics was evaporated and recrystallization from methanol gave 360 mg of (20R)-11β,17,20-trihydroxy-3-oxo-1,4-pregnadien-21-oic acid as white prism, m.p.=213°-214° C. 1H-NMR (Me2SO-6) δ1.03(s,3H,13-CH3), 1.39(s,3H,10-CH3), 3.94(s,1H,20-H), 4.19(m,1N,11-H), 5.90(s,1H,4-H), 6.13(dd,1H,J=10 and 2 Hz,2-H), 7.31(d,1H,J=10 Hz,2-H), 8.30(s,1H,20-COOH).

Workup

  1. additionwas added
  2. extractionAfter extracting with ethyl acetate (300 ml)
  3. customthe organics was evaporated
  4. customrecrystallization from methanol

Sources & evidence

ORD record
ord-ba5c4b3766444980b4b368d727767fbc
Source dataset
uspto-grants-1993_04
Patent number
US05200518

Linked notes

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