Potassium Carbonate → (4R,5R)-4-Fluoromethyl-5-(4-methanesulfinyl-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1484419Notes

Reaction equation

HRID 1484419 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][F:14])[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[O:10][C:9]1([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:26].[K+].[K+].C1C=C(Cl)C=C(C(OO)=O)C=1>C(O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][F:14])[C@@H:11]([C:15]2[CH:16]=[CH:17][C:18]([S:21]([CH3:22])=[O:26])=[CH:19][CH:20]=2)[O:10][C:9]1([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 117655283(4R,5R)-4-Fluoromethyl-2,2-dimethyl-5-(4-methylsulfanyl-phenyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 117662128(4R,5R)-4-Fluoromethyl-5-(4-methanesulfinyl-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterYield 63.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4R,5R)-4-Fluoromethyl-2,2-dimethyl-5-(4-methylsulfanyl-phenyl)-oxazolidine-3-carboxylic acid tert-butyl ester (6 g, 16.91 mmol) in ethanol (300 mL) is cooled to 0° C. followed by addition of K2CO3 (4.665 g, 33.80 mmol) and m-CPBA (2.90, 16.90 mmol) at 0° C. and resulting reaction mixture is stirred at 0° C. for 10 h. After completion, reaction mixture is quenched with water and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by CombiFlash using 120 g column with 100% ethyl acetate in hexane as an eluent to afford title compound (4 g) as colorless oil. 1H-NMR (400 MHz, DMSO): δ 1.43 (s, 9H), 1.50 (s, 3H), 1.62 (s, 3H), 2.74 (s, 3H), 3.82-3.89 (m, 1H), 4.46-4.57 (m, 1H), 4.81 (m, 1H), 5.15 (d, J=7.28 Hz, 1H), 7.65-7.72 (m, 4H). LC-MS (m/z): M+H=372.3.

Workup

  1. customresulting
  2. customreaction mixture
  3. customAfter completion, reaction mixture
  4. customis quenched with water
  5. extractionextracted with ethyl acetate
  6. dry with materialOrganic layer is dried over sodium sulphate
  7. concentrationconcentrated
  8. custompurified by CombiFlash

Sources & evidence

ORD record
ord-277b8eda108d483ea86d2eaab89105ed
Source dataset
uspto-grants-2016_08
Patent number
US09422236B2

Reaction notes

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