Hydrochloric Acid → (2R,3S)-2-amino-3-(benzyloxy)-4,4,4-trifluorobutanoic acid hydrochloride salt

HRID 238576

Reaktionsgleichung

Reaktionsgleichung von HRID 238576
[CH2:1]([O:8][C@H:9]([C:22]([F:25])([F:24])[F:23])[C@@H:10]([NH:14]C(OC(C)(C)C)=O)[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:26]>CCOC(C)=O>[ClH:26].[NH2:14][C@H:10]([C@H:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:22]([F:24])([F:25])[F:23])[C:11]([OH:13])=[O:12]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 58035704(2R,3S)-2-(tert-Butoxycarbonylamino)-3-(benzyloxy)-4,4,4-trifluorobutanoic acid

Produkt 1

HCID 49800574(2R,3S)-2-amino-3-(benzyloxy)-4,4,4-trifluorobutanoic acid hydrochloride saltAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of (2R,3S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)-4,4,4-trifluorobutanoic acid (1.56 g, 4.2 mmol) in EtOAc (30 mL) was added EtOAc saturated with hydrogen chloride (30 mL) at 0° C. Then, the mixture was stirred at room temperature for 1.5 h. After concentration of the reaction mixture to about 15 mL, the white solid was collected by filtration and washed with EtOAc, dried in vacuum to give the title compound (2R,3S)-2-amino-3-(benzyloxy)-4,4,4-trifluorobutanoic acid hydrochloride salt (1.06 g, 84% for two steps). 1H NMR (400 MHz, CD3OD, δ in ppm) 7.32˜7.44 (m, 5H), 4.86 (d, J=2.0 Hz, 2H), 4.70 (dq, J=3.6, 6.6 Hz, 1H), 4.50 (d, J=3.6 Hz, 1H).

Aufarbeitung

  1. filtrationAfter concentration of the reaction mixture to about 15 mL, the white solid was collected by filtration
  2. washwashed with EtOAc
  3. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-050d1ef4519a4eb4abb6c3f1a88031c6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642632B2

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