Stannous chloride dihydrate → 2-[(2-Aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acid, tert-butyl ester

HRID 1420583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1420583
[OH:1][CH2:2][CH:3]([N:11]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-])=O)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].O.O.Cl[Sn]Cl>CO>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][N:11]([S:22]([C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)(=[O:24])=[O:23])[CH:3]([CH2:2][OH:1])[C:4]([O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:5]

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 86755435HCID 86755435, Verbindung

Produkt 1

HCID 867554362-[(2-Aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acid, tert-butyl esterAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 0.60 g (1.28 mmol) of 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-nitrobenzyl)amino]propionic acid, tert-butyl ester and 1.45 g (6.45 mmol) of SnCl2.2H2O in 20 ml of methanol was heated in an oil bath at 90° C. for 2 hours. The solvent was removed under vacuum and ethyl acetate added to the residue. The mixture was neutralized with saturated sodium bicarbonate solution and filtered through diatomaceous earth. The ethyl acetate layer was separated and washed with H2O, brine and dried with Na2SO4. The solvent was removed under vacuum to give 0.30 g (53%) of a gum. Anal. for C21H28N2O6S: Calc'd: C, 57.8; H,6.5; N,6.4; Found: C, 57.8; H,7.0; N,6.2.

Aufarbeitung

  1. customThe solvent was removed under vacuum and ethyl acetate
  2. additionadded to the residue
  3. filtrationfiltered through diatomaceous earth
  4. customThe ethyl acetate layer was separated
  5. washwashed with H2O, brine
  6. dry with materialdried with Na2SO4
  7. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-debbb659cd4c48a0b6a34518f563c417
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071903

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