Hydrochloric Acid → 4-(((1r)-3-Hydroxy-1-((phenylthio)methyl)propyl)amino)-3-nitrobenzenesulfonamide

HRID 2085762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085762
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C@@H:12]([CH2:17][S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][C:14](O)=[O:15])=[C:7]([N+:25]([O-:27])=[O:26])[CH:6]=1)(=[O:4])=[O:3].B.CO.Cl>C1COCC1.C(OCC)(=O)C>[OH:15][CH2:14][CH2:13][C@@H:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([NH2:1])(=[O:4])=[O:3])=[CH:6][C:7]=1[N+:25]([O-:27])=[O:26])[CH2:17][S:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 11683013(r)-3-(2-Nitro-4-sulfamoylphenylamino)-4-(phenylthio)butanoic acid

Produkt 1

HCID 684535934-(((1r)-3-Hydroxy-1-((phenylthio)methyl)propyl)amino)-3-nitrobenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of Example 122E (206 mg, 0.50 mmol) and 1M borane in THF (20 mL) was stirred for 16 hours, treated sequentially with methanol (5.0 mL) and 1N HCl (2.0 mL), diluted with ethyl acetate (50 mL), washed with water (2 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated The concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/dichloromethane to provide the desired product. MS (ESI(+)) m/e 398 (M+H)+.

Aufarbeitung

  1. washwashed with water (2 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated The concentrate
  5. customwas purified by flash column chromatography on silica gel with 20-50% ethyl acetate/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-2d6f9a8be1ff469ebac05022131b91ef
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720338B2

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