(S)-4-Benzyl-2-oxazolidinone → HCID 68847527, 화합물

HRID 1786108노트

반응식

HRID 1786108 반응식
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[C:19](Cl)(=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26]>C1COCC1>[C:19]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])(=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26]

참가 물질

5

반응물 3

HCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 111056577-Octenoyl chlorideHCID 178418339Butyllithium

생성물 1

HCID 68847527HCID 68847527, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
10 °C

실험 절차

To a solution of (S)-(-)-4-benzyl-2-oxazolidinone (12.4 g, 69.79 mmol) in THF (200 mL) at −78° C. was added dropwise n-BuLi (30.7 mL, 2.5M solution in hexane, 76.77 mmol). After stirring for 30 min at the same temperature, the reaction mixture was then treated with 7-octenoyl chloride (11.21 g, 69.79 mmol). The reaction mixture was stirred and allowed to warm to 10° C. over 5 h, and then quenched with saturated aqueous NH4Cl solution (200 mL). The aqueous layer was extracted with EtOAc (200 mL×2). The combined organic layers were washed with brine, and dried over MgSO4. Removal of the solvent under reduced pressure yielded the title compound. MH+302.

후처리

  1. stirringThe reaction mixture was stirred
  2. customquenched with saturated aqueous NH4Cl solution (200 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (200 mL×2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-d1b03ab1bb2c4894a946937823c213bd
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507726B2

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