Tetrahydrofuran → (S)-4-(3-chlorophenyl)oxazolidin-2-one

HRID 539115노트

반응식

HRID 539115 반응식
Cl.[NH2:2][C@@H:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)[CH2:4][OH:5].[OH-].[K+].C1C[O:18][CH2:17]C1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O.CCOC(C)=O>[Cl:12][C:8]1[CH:7]=[C:6]([C@H:3]2[CH2:4][O:5][C:17](=[O:18])[NH:2]2)[CH:11]=[CH:10][CH:9]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 94429TriphosgeneHCID 67034221(S)-2-amino-2-(3-chlorophenyl)ethanol hydrochloride

생성물 1

HCID 67033385(S)-4-(3-chlorophenyl)oxazolidin-2-one수율 58.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of (S)-2-amino-2-(3-chlorophenyl)ethanol hydrochloride (500 mg, 2.40 mmol) in water (12 mL) at 0° C. was added potassium hydroxide (809 mg, 14.4 mmol) followed by THF (12 mL) and the reaction was stirred at 0° C. for 20 minutes. Triphosgene (713 mg, 2.40 mmol) was added and the reaction was stirred at 0° C. for 2 hours. The reaction was poured into EtOAc and the organic phase washed with 1N HCl, 1N NaOH and brine. After drying over MgSO4, concentration yielded (S)-4-(3-chlorophenyl)oxazolidin-2-one (278 mg, 58.5% yield) as an oil.

후처리

  1. stirringthe reaction was stirred at 0° C. for 2 hours
  2. washthe organic phase washed with 1N HCl, 1N NaOH and brine
  3. dry with materialAfter drying over MgSO4, concentration

출처 및 근거

ORD 기록
ord-16a8dd164b1d43bfab7ac930fe96c913
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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