Hydrogen Peroxide → HCID 58388234, compound

HRID 2047349Notes

Reaction equation

HRID 2047349 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([C:23](=[O:37])N2[C@H](CC3C=CC=CC=3)COC2=O)[CH2:11][NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=[CH:6][C:7]=1[F:8].[OH:38]O.[Li+].[OH-]>O1CCCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@@H:10]([CH2:11][NH:12][C:13]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:22])[C:23]([OH:37])=[O:38])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 58388237HCID 58388237, compound

Product 1

HCID 58388234HCID 58388234, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of phenylmethyl {(2S)-2-[(3,4-difluorophenyl)methyl]-3-oxo-3-[(4R)-2-oxo-4-(phenylmethyl)-1,3-oxazolidin-3-yl]propyl}carbamate (548 mg, 1.078 mmol) in tetrahydrofuran (16.200 ml) and Water (5.40 ml) at 0° C. was added H2O2 (0.198 ml, 1.940 mmol)[30 wt %] followed by LiOH (2.69 ml, 2.155 mmol)[0.8M solution]. After 1 h, the solution warmed to 25° C. and stirred 2 h. The reaction mixture was quenched with Na2SO3 solution and the pH was carefully adjusted to ˜3 with 2N HCl solution. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified by column chromatography (10-60% EtOAc in hexanes) affording (2S)-3-(3,4-difluorophenyl)-2-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]propanoic acid (260 mg, 0.700 mmol, 64.9% yield) as a clear oil: LCMS (ES) m/e 350 (M+H)+, 1H NMR (400 MHz, DMSO-d6) δ ppm 12.36 (br. s., 1 H) 7.20-7.40 (m, 8 H) 7.03 (br. s., 1 H) 5.02 (s, 2 H) 4.52-4.75 (m, 1 H) 3.01-3.26 (m, 2 H) 2.77 (s, 2 H).

Workup

  1. customThe reaction mixture was quenched with Na2SO3 solution
  2. washThe aqueous phase was washed several times with DCM
  3. dry with materialthe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography (10-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-174aa12aefe44c14b9924c50b46bd1c6
Source dataset
uspto-grants-2013_11
Patent number
US08592475B2

Reaction notes

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