Hydrogen Peroxide → (S)-3-((Tert-butoxycarbonyl)amino)-2-(4-chlorobenzyl)propanoic acid

HRID 1192347Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C@H:9]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:10](N1[C@H](C)[C@H](C2C=CC=CC=2)OC1=O)=[O:11])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].OO.[O-:38]S([O-])=O.[Na+].[Na+]>C1COCC1.O.CCOC(C)=O>[C:1]([O:5][C:6]([NH:7][CH2:8][C@H:9]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:10]([OH:11])=[O:38])=[O:33])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [(2S)-2-(4-Chlorobenzyl)-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-propyl]-carbamic acid tert-butyl ester (300 mg, 0.63 mmol) in THF/H2O (30/10 mL) at 0° C. was added LiOH (80 mg, 1.9 mmol) and H2O2 (30% by volume, 3.0 mL, 0.63 mmol) and stirred at 0° C. for 30 minutes. Then Na2SO3 (saturated solution, 10 mL) was added slowly & cautiously. Diluted with EtOAc (100 mL) and extracted into water (2×100 mL) The aq. layer was acidified (1N HCl) and extracted into EtOAc (3×100 mL) Dried over Na2SO4 and concentrated in vacuo to give (S)-2-(tert-Butoxycarbonylamino-methyl)-3-(4-chlorophenyl)-propionic acid (150 mg, 75%.) LCMS (APCI−) m/z 322 [M-Boc+H]−; Rt: 2.23 min

Workup

extractionextracted into water (2×100 mL) The aq. layer
extractionextracted into EtOAc (3×100 mL)
dry with materialDried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d2158fdc9fda415b87813efedfb9eaab
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680114B2

Reaction notes

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