Stannous chloride dihydrate → Methyl cis(+/-)-2-amino-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate

HRID 43804

Reaktionsgleichung

[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[CH:20][C:21]([N+:28]([O-])=O)=[C:22]([CH:27]=2)[C:23]([O:25][CH3:26])=[O:24])[CH2:14][C@H:13]1[O:31][CH3:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C.C1COCC1>[NH2:28][C:21]1[CH:20]=[CH:19][C:18]([N:15]2[CH2:16][CH2:17][C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[C@H:13]([O:31][CH3:32])[CH2:14]2)=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

Methyl cis(±)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-nitrobenzoate obtained in Example (185a) was dissolved in ethanol (20 ml) and THF (20 ml). Tin (II) chloride dihydrate (4.4 g, 19.6 mmol) was added, and the mixture was stirred at 75° C. overnight. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with aqueous sodium bicarbonate and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, 900 mg of the title compound was obtained as an oily substance.

Aufarbeitung

concentrationThe reaction solution was concentrated under reduced pressure
additiondiluted with ethyl acetate
washwashed with aqueous sodium bicarbonate and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-6b102dd6d17a4d5abbb6cc0bb1f9f2a4
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536197B2

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