Trifluoroacetic acid → 2-[(2-Aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acid

HRID 1420584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1420584
[NH2:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:6]([CH2:14][OH:15])[C:7]([O:9]C(C)(C)C)=[O:8].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:6]([CH2:14][OH:15])[C:7]([OH:9])=[O:8]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 867554362-[(2-Aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acid, tert-butyl ester

Produkt 1

HCID 186128792-[(2-Aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acidAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 0.75 g (1.72 mmol) of 2-[(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acid, tert-butyl ester and 6 ml of trifluoroacetic acid in 6 ml of CH2Cl2 was stirred at room temperature for 3 hours and then concentrated to dryness under vacuum. To the residue was added H2O, CH2Cl2 and 1N NaOH until the aqueous layer reached pH 8. The aqueous layer was then separated, acidified with 2 N citric acid and extracted with ethyl acetate. The extract was washed with H2O, brine and dried Na2SO4. The solvent was removed under vacuum to give 0.35 g (54%) of a solid. Anal. for C17H20N2O6S: Calc'd: C, 53.7; H,5.3; N,7.4; Found: C, 53.0; H,5.3; N,6.9.

Aufarbeitung

  1. concentrationconcentrated to dryness under vacuum
  2. additionTo the residue was added H2O, CH2Cl2 and 1N NaOH until the aqueous layer
  3. customThe aqueous layer was then separated
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with H2O, brine and dried Na2SO4
  6. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a687ba07014740688fe2142c241d625a
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071903

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