Acetone → (2R,3S)-2-(tert-Butoxycarbonylamino)-3-(benzyloxy)-4,4,4-trifluorobutanoic acid

HRID 238575Notes

Reaction equation

[CH2:1]([O:8][C@H:9]([C:21]([F:24])([F:23])[F:22])[C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:27]>>[CH2:1]([O:8][C@H:9]([C:21]([F:23])([F:22])[F:24])[C@@H:10]([NH:13][C:14]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:20])[C:11]([OH:27])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 180Acetone

HCID 49800573(2S,3S)-2-(tert-Butoxycarbonylamino)-3-(benzyloxy)-4,4,4-trifluoro-1-butanol

Product 1

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

Procedure

To a solution of tert-butyl (2S,3S)-3-(benzyloxy)-4,4,4-trifluoro-1-hydroxybutan-2-ylcarbamate (1.47 g, 4.2 mmol) in acetone (80 mL) was added Jone's reagent (8.2 mL) at 0° C. The mixture was stirred at the same temperature for 3 h until the starting material was completely consumed, then the reaction was quenched by adding isopropanol (5 mL). The reaction mixture was extracted with EtOAc. The extracts were washed with water, brine and dried over Na2SO4. Removal of the solvent gave the crude (2R,3S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)-4,4,4-trifluorobutanoic acid (1.56 g), which was used directly for the following reaction. 1H NMR (400 MHz, CD3OD, δ in ppm) 7.25˜7.34 (m, 5H), 4.76 (d, J=10.9 Hz, 1H), 4.70 (d, J=10.9 Hz, 1H), 4.53 (d, J=6.4 Hz, 1H), 4.32 (m, 1H), 1.41 (s, 9H).

Workup

customwas completely consumed
customthe reaction was quenched
additionby adding isopropanol (5 mL)
extractionThe reaction mixture was extracted with EtOAc
washThe extracts were washed with water, brine
dry with materialdried over Na2SO4
customRemoval of the solvent

Sources & evidence

ORD record: ord-12daef46ef79468daa8932f148b6ae49
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642632B2

Reaction notes

Loading…