Hydrochloric Acid → 3-(2-tert-Butoxycarbonyl-ethylsulfamoyl)-benzoic acid methyl ester

HRID 386713

Reaktionsgleichung

Reaktionsgleichung von HRID 386713
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:4])=[O:3].Cl.[NH2:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].Cl>N1C=CC=CC=1>[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:12]=[CH:13][CH:14]=[C:5]([S:2](=[O:4])(=[O:3])[NH:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:6]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 113339Benzoic acid, 3-(chlorosulfonyl)-, methyl esterHCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Produkt 1

HCID 667978353-(2-tert-Butoxycarbonyl-ethylsulfamoyl)-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

To a stirred solution of methyl 3-(chlorosulfonyl)benzoate (5.0 g, 21.31 mmol) in pyridine (50 ml), was added dropwise a solution of tert-butyl 3-aminopropanoate hydrochloride (5.11 g, 23.44 mmol) in pyridine (10 ml) at 0° C. The resulting solution was allowed to warm to RT and stirred for 4 h. 1N HCl (50 ml) was added to the reaction mixture and the aqueous phase was separated and extracted with DCM (3×20 ml). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to afford a viscous amber oil. Purification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the title compound as a colourless oil. 1H NMR (400 MHz, CDCl3) δ 8.53 (1H, s), 8.27 (1H, d), 8.08 (1H, d), 7.63 (1H, t) 5.38 (1H, t), 3.97 (3H, s), 3.20 (2H, m), 2.48 (2H, t), 1.43 (9H, s).

Aufarbeitung

  1. customthe aqueous phase was separated
  2. extractionextracted with DCM (3×20 ml)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford a viscous amber oil
  6. customPurification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-fa88b3d719684d9c8ce61b0904b53a87
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372845B2

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