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

HRID 1589963

反応式

HRID 1589963 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ba5c4b3766444980b4b368d727767fbc
出典データセット
uspto-grants-1993_04
特許番号
US05200518

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