Water → 4-(4-{[(Benzyloxy)carbonyl]amino}butyl)benzoic acid

HRID 1070545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070545
C(=O)([O-])O.[Na+].[NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.O.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C1COCC1>[CH2:25]([O:24][C:22]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 221799734-(4-Aminobutyl)benzoic acid

Produkt 1

HCID 221799644-(4-{[(Benzyloxy)carbonyl]amino}butyl)benzoic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydrogencarbonate (0.95 g, 11.32 mmol) was added into a suspension of 30 in THF (120 mL), followed by water (10 mL), affording a clear solution. Benzyl chloroformate (1.21 mL, 8.49 mmol) was then added into the reaction mixture at 0° C. The reaction mixture was then stirred at room temperature overnight. After that, the solvent was removed under reduced pressure. Ethyl acetate (70 mL) was added to the residue and the solution was washed with 2N HCl (2×30 mL) and water (2×50 mL), then dried in vacuum. 1.82 g (98%) of 31 was obtained as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.11 (m, 2H), 1.28 (m, 2H), 2.33 (m, 2H), 3.02 (m, 2H), 5.01 (m, 2H), 7.15 (m, 7H), 7.93 (d 2H).

Aufarbeitung

  1. customaffording a clear solution
  2. customAfter that, the solvent was removed under reduced pressure
  3. additionEthyl acetate (70 mL) was added to the residue
  4. washthe solution was washed with 2N HCl (2×30 mL) and water (2×50 mL)
  5. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-47ab023c508247ada98398568744e6f4
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903105B2

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