Cortisol → (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methylbutyric acid [11beta,17,21-trihydroxy-3,20-dioxo-pregn-4-en-21-yl] ester

HRID 53065

반응식

HRID 53065 반응식
[CH3:1][C@@:2]12[C@H:12]3[C@@H:13]([OH:26])[CH2:14][C@:15]4([CH3:25])[C@@:19]([OH:24])([C:20]([CH2:22][OH:23])=[O:21])[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C:8]1=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2.[C:27]([O:31][C:32]([NH:34][C@H:35]([C:39]([OH:41])=[O:40])[CH:36]([CH3:38])[CH3:37])=[O:33])([CH3:30])([CH3:29])[CH3:28].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[OH:26][C@H:13]1[CH2:14][C@@:15]2([CH3:25])[C@@H:16]([CH2:17][CH2:18][C@:19]2([OH:24])[C:20](=[O:21])[CH:22]([O:41][C:39](=[O:40])[C@@H:35]([NH:34][C:32]([O:31][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:33])[CH:36]([CH3:37])[CH3:38])[OH:23])[C@H:11]2[C@H:12]1[C@:2]1([CH3:1])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]1

참가 물질

6

반응물 3

HCID 5754CortisolHCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-Valine

생성물 1

HCID 86750657(2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methylbutyric acid [11beta,17,21-trihydroxy-3,20-dioxo-pregn-4-en-21-yl] ester수율 51%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A solution of 3.63 g (10 mmol) of hydrocortisone in 150 ml of dichloromethane is mixed with 2.34 g (10.8 mmol) of N-(tert -butoxycarbonyl)-valine, 500 mg (4.1 mmol) of 4-dimethylaminopyridine and 3.1 g (15 mmol) of dicyclohexylcarbodiimide. The solution is stirred for 3 hours at room temperature, the precipitate that is produced is suctioned off and washed with dichloromethane. The filtrate is concentrated by evaporation in a vacuum. The chromatography on silica gel (hexane→hexane/ethyl acetate 1:1) provides 2.87 g (51%) of (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methylbutyric acid [11β,17,21-trihydroxy-3,20-dioxo-pregn-4-en-21-yl] ester. Crystallization from dichloromethane/diisopropyl ether.

후처리

  1. customthe precipitate that is produced
  2. washwashed with dichloromethane
  3. concentrationThe filtrate is concentrated by evaporation in a vacuum

출처 및 근거

ORD 기록
ord-a60f758833af4ae5911eeed9ebfd2328
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616573

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