Methyl iodide → (R)-3-((2R,3R)-2,3-Dimethyl-hexanoyl)-4-phenyl-oxazolidin-2-one

HRID 349799

반응식

HRID 349799 반응식
[Na].[CH3:2][C@H:3]([CH2:19][CH2:20][CH3:21])[CH2:4][C:5]([N:7]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][O:9][C:8]1=[O:18])=[O:6].[CH3:22]I>C1COCC1>[CH3:22][C@H:4]([C@H:3]([CH3:2])[CH2:19][CH2:20][CH3:21])[C:5]([N:7]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][O:9][C:8]1=[O:18])=[O:6]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 68955002(R)-3-((R)-3-Methyl-hexanoyl)-4-phenyl-oxazolidin-2-one

생성물 1

HCID 69191263(R)-3-((2R,3R)-2,3-Dimethyl-hexanoyl)-4-phenyl-oxazolidin-2-one수율 56.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a 1M THF solution of Sodium hexamethyldisylamide (16.2 g, 88.3 mmol) at −78° C. was added via canular a 0° C. solution of (R)-3-((R)-3-methyl-hexanoyl)-4-phenyl-oxazolidin-2-one (18.7 g, 67.9 mmol) in 70 mL dry THF. The resulting solution was stirred at −78° C. for 30 minutes. Methyl Iodide (48.2 g, 339.5 mmol) was added and stirring at −78° C. was continued for 4 hours. The reaction was quenched with saturated ammonium chloride solution, extracted into CH2Cl2 and washed with 1M sodium Bisulfite. The solution was dried over MgSO4, concentrated and chromatographed in 10% ethylacetate in hexane to give the titled compound (11.1 g, 56.5% yield) as an oil. MS, m/z (relative intensity): 1H NMR (400 MHz, CDCl3) δ ppm 0.8 (t, J=7.0 Hz, 3 H) 0.9 (d, J=6.6 Hz, 3 H) 1.0 (d, J=6.8 Hz, 3 H) 1.0 (d, J=8.5 Hz, 1H) 1.1 (m, 1 H) 1.4 (m, 1 H) 1.7 (m, 1 H) 3.7 (m, 1 H) 4.2 (dd, J=8.8, 3.4 Hz, 1 H) 4.6 (t, J=8.7 Hz, 1 H) 5.4 (dd, J=8.7, 3.3 Hz, 1 H) 7.2 (m, 2 H) 7.3 (m, 3 H). MS, m/z (relative intensity):290 [M+1H, 100%].

후처리

  1. stirringstirring at −78° C.
  2. waitwas continued for 4 hours
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. extractionextracted into CH2Cl2
  5. washwashed with 1M sodium Bisulfite
  6. dry with materialThe solution was dried over MgSO4
  7. concentrationconcentrated
  8. customchromatographed in 10% ethylacetate in hexane

출처 및 근거

ORD 기록
ord-7aa9db90007b496c8fdf90fb7e1eaeeb
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179934B2

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