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

HRID 1589963노트

반응식

HRID 1589963 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178942Methyl (11beta,20R)-11,17,20-trihydroxy-3-oxopregna-1,4-dien-21-oate2회

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-ba5c4b3766444980b4b368d727767fbc
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05200518

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