Hydrochloric Acid → (R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide

HRID 471342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471342
[CH2:1]([O:8][C:9]([NH:11][C@@:12]([C:24](=[O:26])[NH2:25])([CH2:18][C:19](OCC)=[O:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+].Cl>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@:12]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:18][C:19](=[O:20])[NH:25][C:24]1=[O:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 66725151(R)-diethyl 2-benzyloxycarbonylamino-2-carbamoylsuccinate

Produkt 1

HCID 9944916(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimideAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of (R)-diethyl 2-benzyloxycarbonylamino-2-carbamoylsuccinate (200 mg) in dehydrated ethanol (10 mL) was added with sodium ethoxide (41 mg) with ice cooling and stirring, the mixture was stirred at the same temperature for 2 hours, then cold 1 mol/L hydrochloric acid was poured into the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate/n-hexane to obtain the title compound (149 mg, yield: 85%) as colorless crystals. Optical rotation [α]D28 was −31.8° (c 0.59, ethanol), and optical purity was 99.2% ee.

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was recrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-dea6f48a967d40ce8d976c61eae7cf13
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633001B2

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