Ethyl 2-{[(benzyloxy)carbonyl]imino}-3,3,3-trifluoropropanoate → N-(Benzyloxycarbonyl)-3,3,3-trifluoroalanine ethyl ester

HRID 58899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58899
[CH2:1]([O:8][C:9]([N:11]=[C:12]([C:18]([F:21])([F:20])[F:19])[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.[BH4-].[Na+]>C(OCC)C>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:18]([F:19])([F:21])[F:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 2758803Ethyl 2-{[(benzyloxy)carbonyl]imino}-3,3,3-trifluoropropanoateHCID 4311764Sodium borohydride

Produkt 1

HCID 562278N-(Benzyloxycarbonyl)-3,3,3-trifluoroalanine ethyl esterAusbeute 48,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(benzyloxycarbonylimino)-3,3,3-trifluoropropanoate (45.0 g, 148.5 mmol) in diethyl ether (300 mL) was added sodium borohydride (11.3 g 297 mmol) in portions at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h. The reaction was quenched with water (100 mL) carefully and the organic layer was separated. The aqueous layer was extracted with EtOAc (100 mL×3). The organic layers were combined, washed with brine (200 mL×2), dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/petroleum ether=1:9) to afford ethyl 2-(benzyloxycarbonylamino)-3,3,3-trifluoropropanoate (22.0 g, 48% yield).

Aufarbeitung

  1. customThe reaction was quenched with water (100 mL) carefully
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with EtOAc (100 mL×3)
  4. washwashed with brine (200 mL×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel (EtOAc/petroleum ether=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-9415beac30574252947e509ec9035b64
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434761B2

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