Hydrochloric Acid → HCID 16116512, Verbindung

HRID 716531

Reaktionsgleichung

Reaktionsgleichung von HRID 716531
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[CH2:17]([O:19][C:20](Cl)=[O:21])[CH3:18].Cl>C1COCC1.O>[CH2:17]([O:19][C:20]([NH:11][C@H:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:8]([OH:10])=[O:9])=[O:21])[CH3:18]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 70134Phenylglycine, D-HCID 516892Sodium Bicarbonate

Produkt 1

HCID 16116512HCID 16116512, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

D-Phenylglycine (R) (85.2 mmol) was dissolved in anhydrous THF (260 mL) with NaHCO3 (256 mmol) in water (260 mL). Ethylchloroformate (0.235 mol) was added. After stirred at room temperature overnight, the reaction mixture was acidified to pH 3 with 1N HCl. The aqueous layer was extracted with EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to give (R)-2-(ethoxycarbonylamino)-2-phenylacetic acid 41 as a white solid in 82% yield. MS (ESI, EI+) m/z=224.2 (MH+).

Aufarbeitung

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bba26de7fa1342eebe2c279c560c5a4d
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187496B2

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