Ethyl Acetate → HCID 89814220, compound

HRID 525355Notes

Reaction equation

HRID 525355 reaction equation
[CH2:1]([C:3]([OH:21])([CH2:19][CH3:20])[C@H:4]([NH:11][C:12](=[O:18])OC(C)(C)C)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:2].CC(C)([O-])C.[K+].CCOC(C)=O>C1COCC1.CCCCCC>[CH2:19]([C:3]1([CH2:1][CH3:2])[O:21][C:12](=[O:18])[NH:11][C@H:4]1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH3:20]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 89827530HCID 89827530, compound

Product 1

HCID 89814220HCID 89814220, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of (R)-tert-butyl (2-ethyl-2-hydroxy-1-phenylbutyl)carbamate (1.2 g, mmol) in dry THF (5 mL) in a 25 mL round bottom flas was cooled to 0° C. To the solution was added potassium t-butoxide (1.46 g, 13.04 mmol) in one portion, and the mixture was allowed to slowly warm to room temperature and stirred for 2 hours. After completion of reaction (monitored by TLC, TLC eluent: 30% EtOAc in hexane), the solvent was removed under reduced pressure, the reaction was quenched in saturated NH4Cl solution. The product was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated to afford 0.6 g (66.6%) of (S)-5,5-diethyl-4-phenyloxazolidin-2-one colorless oil. 1H NMR (300 MHz, CDCl3) δ: 7.38-7.33 (m, 3H), 7.28-7.25 (m, 2H), 5.63 (s, 1H), 4.71 (s, 1H), 1.80-1-2 (m, 2H), 1.38-1.28 (m, 1H), 1.06 (t, J=7.2 Hz, 3H), 0.72 (t, J=7.4 Hz, 3H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe reaction was quenched in saturated NH4Cl solution
  3. extractionThe product was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-33ed14c9731c4894a048778745ce78c4
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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