m-Chloroperbenzoic acid → di-tert-Butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)-1-oxidopyridin-2-yl]methyl}-L-glutamate

HRID 591308노트

반응식

HRID 591308 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][F:29])=[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:42]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][F:29])=[CH:22][N+:21]=1[O-:42])[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 70674548Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}-L-glutamate

생성물 1

HCID 117812666di-tert-Butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)-1-oxidopyridin-2-yl]methyl}-L-glutamate수율 94.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 350 mg di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}-L-glutamate (0.68 mmol; see Example 17d) in dichloromethane (5 mL) was added 185 mg meta-chloro peroxybenzoic acid (70%), and the mixture was stirred for 1 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 concentrated in vacuo, and the residue was purified by preparative HPLC (Method D) to give 340 mg of the target compound (93% yield).

후처리

  1. extractionThe mixture was extracted with aqueous sodium bicarbonate
  2. extractionfollowed by re-extraction of the aqueous layer with dichloromethane
  3. concentrationThe combined organic layers were concentrated in vacuo
  4. customthe residue was purified by preparative HPLC (Method D)

출처 및 근거

ORD 기록
ord-108fbad314594c09b4ad8cdc8c1f2177
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238631B2

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