Triethylamine → (R)-4-((S)-1-fluoroethyl)-3-(4-methoxybenzyl)oxazolidin-2-one

HRID 57481

반응식

HRID 57481 반응식
O[C@@H:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH3:3].C(N(CC)CC)C.[F:26]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F>CC#N.O>[F:26][C@H:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH3:3]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 90423794(R)-4-((R)-1-hydroxyethyl)-3-(4-methoxybenzyl)oxazolidin-2-one

생성물 1

HCID 90423361(R)-4-((S)-1-fluoroethyl)-3-(4-methoxybenzyl)oxazolidin-2-one수율 95.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

To a cooled (0° C.) solution of (R)-4-((R)-1-hydroxyethyl)-3-(4-methoxybenzyl)oxazolidin-2-one (2.27 g, 9.04 mmol) in 30 mL MeCN were added triethylamine (11.4 mL, 82 mmol) followed by perfluoro-1-butanesulfonyl fluoride (4.9 mL, 27.3 mmol) and NEt3(HF)3 (4.5 mL, 27.6 mmol) and the resulting mixture was stirred at 0° C. for 70 min. The reaction mixture was diluted with water (60 mL) and extracted with EtOAc (3×60 mL). Combined organics were washed with water (70 mL), brine (70 mL), dried over Na2SO4, filtered and concentrated. Flash column chromatography (EtOAc/heptane 5 to 70%) gave 2.19 g of the desired product. 1H NMR (400 MHz, CDCl3) δ 7.25-7.20 (m, 2H), 6.92-6.83 (m, 2H), 4.87 (d, J=15.1 Hz, 1H), 4.75 (dqd, J=47.6, 6.6, 2.1 Hz, 1H), 4.26 (td, J=9.2, 1.4 Hz, 1H), 4.17-4.05 (m, 2H), 3.81 (s, 3H), 3.71 (dddd, J=19.8, 9.5, 5.8, 2.1 Hz, 1H), 1.29 (dd, J=23.1, 6.2 Hz, 3H). MS m/z 254.5 (M+H).

후처리

  1. extractionextracted with EtOAc (3×60 mL)
  2. washCombined organics were washed with water (70 mL), brine (70 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-96603c1f4c5f430881a7755aa85f9557
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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