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

HRID 238576

Reaction equation

HRID 238576 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-050d1ef4519a4eb4abb6c3f1a88031c6
Source dataset
uspto-grants-2014_02
Patent number
US08642632B2

Linked notes

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