Dimethyl Sulfate → Methyldigoxin

HRID 746252

반응식

HRID 746252 반응식
[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:14]([OH:15])[CH2:13][C@H:12]([O:16][C@H:17]3[C@@H:22]([OH:23])[CH2:21][C@H:20]([O:24][C@@H:25]4[CH2:30][C@H:29]5[CH2:31][CH2:32][C@H:33]6[C@@:38]7([OH:48])[CH2:39][CH2:40][C@H:41]([C:42]8[CH2:47][O:46][C:44](=[O:45])[CH:43]=8)[C@@:37]7([CH3:49])[C@H:36]([OH:50])[CH2:35][C@@H:34]6[C@@:28]5([CH3:51])[CH2:27][CH2:26]4)[O:19][C@@H:18]3[CH3:52])[O:11][C@@H:10]2[CH3:53])[CH2:5][C@H:4]([OH:54])[C@@H:3]1[OH:55].O.O.O.O.O.O.O.O.[OH-].[Sr+2].[OH-].S([O:72][CH3:73])(OC)(=O)=O>>[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:14]([OH:15])[CH2:13][C@H:12]([O:16][C@H:17]3[C@@H:22]([OH:23])[CH2:21][C@H:20]([O:24][C@@H:25]4[CH2:30][C@H:29]5[CH2:31][CH2:32][C@H:33]6[C@@:38]7([OH:48])[CH2:39][CH2:40][C@H:41]([C:42]8[CH2:47][O:46][C:44](=[O:45])[CH:43]=8)[C@@:37]7([CH3:49])[C@H:36]([OH:50])[CH2:35][C@@H:34]6[C@@:28]5([CH3:51])[CH2:27][CH2:26]4)[O:19][C@@H:18]3[CH3:52])[O:11][C@@H:10]2[CH3:53])[CH2:5][C@H:4]([OH:54])[C@@H:3]1[OH:55].[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:14]([OH:15])[CH2:13][C@H:12]([O:16][C@H:17]3[C@@H:22]([OH:23])[CH2:21][C@H:20]([O:24][C@@H:25]4[CH2:30][C@H:29]5[CH2:31][CH2:32][C@H:33]6[C@@:38]7([OH:48])[CH2:39][CH2:40][C@H:41]([C:42]8[CH2:47][O:46][C:44](=[O:45])[CH:43]=8)[C@@:37]7([CH3:49])[C@H:36]([OH:50])[CH2:35][C@@H:34]6[C@@:28]5([CH3:51])[CH2:27][CH2:26]4)[O:19][C@@H:18]3[CH3:52])[O:11][C@@H:10]2[CH3:53])[CH2:5][C@H:4]([OH:54])[C@@H:3]1[O:72][CH3:73]

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 2724385DigoxinHCID 21617461Strontium hydroxide octahydrate

생성물 2

HCID 443946Methyldigoxin수율 72.62%HCID 2724385Digoxin수율 17.16%

실험 절차

A solution of 2.34 g (3 millimoles) of digoxin is treated with 797 mg (3 millimoles) of strontium hydroxide octahydrate and the mixture is methylated with 757 g (6 millimoles) of dimethyl sulfate at 0° C., the procedure being the same as in Example 6. Evaporation of the fractions collected gives 119 mg (4.90% of theory of dimethyldigoxin, 403 mg (17.16%) of digoxin and 1.732 g (72.62% of theory) of β-methyldigoxin, from which 1.59 g of pure β-methyldigoxin are obtained after recrystallization from acetone. The yield is 66.67% and the selectivity of the reaction is 80.48%.

후처리

  1. customEvaporation of the fractions
  2. customcollected

출처 및 근거

ORD 기록
ord-f88a971728074acd92bfd58f34c6e99b
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04603196

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