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 591310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591310
[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]

Komponenten

4

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4eda9d26f2234cb3a6a0fd1d9c7f4781
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238631B2

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