Methyl iodide → Methyl 2-(4(S)-phenyloxazolidin-2-on-3-yl)propanoate

HRID 2207139노트

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HRID 2207139 반응식
[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI>C1COCC1>[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 10609791HCID 10609791, 화합물

생성물 1

HCID 66587141Methyl 2-(4(S)-phenyloxazolidin-2-on-3-yl)propanoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-70 °C

실험 절차

A solution of methyl (4(S)-phenyloxazolidin-2-on-3-yl)acetate (1 g, 4.25 mmol) in 10 mL of anhydrous THF at −78° C. was treated with 4.68 mL (4.68 mmol) of a 1 M solution of lithium bis(trimethylsilyl)amide in THF. The reaction mixture was stirred for 1 h. at about −70° C. before adding MeI (1.59 mL, 25.51 mmol). Upon complete conversion of the azetidinone, the reaction was quenched with saturated aqueous NH4Cl and partitioned between EtOAc and water. The organic layer was washed sequentially with saturated aqueous sodium bisulfite, and saturated aqueous NaCl. The resulting organic layer was dried (MgSO4) and evaporated to afford the title compound (a mixture of diasteromers) as a white solid (1.06 g, 93%); 1H NMR (CDCl3) δ 1.07/1.53 (d/d, J=7.5 Hz, 3H), 3.59/3.74 (s/s, 3H), 3.85/4.48 (q/q, J=7.5 Hz, 1H), 4.10-4.14 (m, 1H), 4.60-4.64/4.65-4.69 (m/m, 1H), 4.88-4.92/4.98-5.02 (m/m, 1H), 7.24-7.40 (m, 5H).

후처리

  1. customUpon complete conversion of the azetidinone, the reaction was quenched with saturated aqueous NH4Cl
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed sequentially with saturated aqueous sodium bisulfite, and saturated aqueous NaCl
  4. dry with materialThe resulting organic layer was dried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-b19ebe7e6ae64e4bb53dec609f388fdf
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376424B2

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