Ethyl Acetate → HCID 89814050, compound

HRID 525348Notes

Reaction equation

HRID 525348 reaction equation
OC(C)(C)[C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])C)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10].CC(C)([O-])C.[K+].CCOC(C)=O>C1COCC1.CCCCCC>[CH3:17][C:14]1([CH3:16])[O:13][C:12](=[O:18])[NH:11][C@H:3]1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 89827451HCID 89827451, compound

Product 1

HCID 89814050HCID 89814050, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of (S)-tert-butyl (2-hydroxy-2-methyl-1-(o-tolyl)propyl)carbamate (1 g, 3.5 mmol) in THF (20 mL) was added potassium tert-butoxide (803.37 mg, 7.1 mmol) at 0-5° C. The resulting reaction mixture was stirred for 2 hours at ambient temperature. After completion of the reaction (monitored by TLC, TLC system: 50% EtOAc in hexane), the reaction mixture was quenched with ice water and extracted with EtOAc. The combined organic layers were washed with, water, washed with saturated NaCl solution, dried with Na2SO4, filtered and evaporated to afford (S)-5,5-dimethyl-4-(o-tolyl)oxazolidin-2-one, 0.7 g (95.28% Y) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.96 (s, 1H), 7.27-7.25 (m, 1H), 7.22-7.19 (m, 3H), 4.83 (s, 1H), 2.29 (s, 3H), 1.55 (s, 3H), 0.81 (s, 3H). m/z (ESI) 206.1 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customthe reaction mixture was quenched with ice water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with, water
  5. washwashed with saturated NaCl solution
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-eb3a8d11acdf48139ae7c40f6f8fbc01
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

Loading…