m-Chloroperbenzoic acid → Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)-1-oxidopyridin-2-yl]methyl}-L-glutamate

HRID 591310ノート

反応式

HRID 591310 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])=[CH:22][N:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:52]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:31])=[O:32])=[CH:22][N+:21]=1[O-:52])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 70675125Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)pyridin-2-yl]methyl}-L-glutamate

生成物 1

HCID 117812700Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)-1-oxidopyridin-2-yl]methyl}-L-glutamate収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 125 mg di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-{[5-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)pyridin-2-yl]methyl}-L-glutamate (0.19 mmol; see Example XB) in dichloromethane (10 mL) was added 51 mg meta-chloro peroxybenzoic acid (70%), and the mixture was stirred for 3 h at room temperature. The mixture was extracted with aqueous sodium bicarbonate, followed by re-extraction of the aqueous layer with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo, and the residue was purified by preparative HPLC. (Method D) to give 104 mg of the target compound as colourless foam (81% yield).

後処理

  1. extractionThe mixture was extracted with aqueous sodium bicarbonate
  2. extractionfollowed by re-extraction of the aqueous layer with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-4eda9d26f2234cb3a6a0fd1d9c7f4781
出典データセット
uspto-grants-2016_01
特許番号
US09238631B2

反応ノート

読み込み中…