Ethyl Acetate → HCID 46837646, 화합물

HRID 1399555노트

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HRID 1399555 반응식
FC(F)(F)S(O[C@H:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])(=O)=O.[NH2:15][C:16](C)([CH3:19])[CH2:17]O.C([O-])(O)=O.[Na+].CCOC(C)=O>C(Cl)Cl>[CH3:12][C@H:7]1[C:8](=[O:9])[O:10][CH2:11][C:16]([CH3:19])([CH3:17])[NH:15]1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 118072-Amino-2-methyl-1-propanolHCID 516892Sodium BicarbonateHCID 11064395Propanoic acid, 2-[[(trifluoromethyl)sulfonyl]oxy]-, methyl ester, (2R)-

생성물 1

HCID 46837646HCID 46837646, 화합물수율 63%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-40 °C

실험 절차

A solution of triflate 14 (5.00 g, 0.021 mol) in anhydrous CH2Cl2 (80 mL) under an N2 atmosphere, was cooled to −40° C. and was treated with a solution of 2-amino-2-methyl-1-propanol (2.5 folds, 4.68 g, 0.0525 mol) in anhydrous CH2Cl2 (10 mL). After stirring for 2 h at −40° C., the reaction mixture was warmed slowly to 0° C. then to room temperature and stirred overnight. The reaction mixture was treated with saturated aqueous NaHCO3 solution (100 mL). The organic phase was washed (water, brine), separated, and dried (Na2SO4). The aqueous layer was extracted with EtOAc (twice). The organic layer was separated, washed (water, brine) and dried (Na2SO4). The organic extracts were combined and concentrated to give a yellow oil. Column chromatography on silica gel using hexanes-EtOAc (1:2) to EtOAc gave 1.88 g (63%) of 15 as a light yellow oil: [α]23D −75° (c 1.0, CHCl3); 1H NMR (CDCl3) δ 4.11 (s, 2H), 3.71 (q, 1H, J=6.8), 1.39 (d, 3H, J=6.8 Hz), 1.26 (s, 3H), 1.18 (s, 3H); 13C NMR (CDCl3) δ 229.2, 77.6, 49.5, 49.3, 27.2, 24.2, 18.4; LCMS (APCI) m/z 144.3 [(M+H)+, M=C7H13NO2]; Anal. (C7H13NO2) calcd: C, 58.72; H, 9.15; N, 9.78. found: C, 58.60; H, 9.35; N, 9.79. Note: 1H NMR data is similar with the data reported in the literature for the racemic compound (Koch, T. H.; Olesen, J. A.; DeNiro, J., J. Am. Chem. Soc. 1975, 97, (25), 7285-7288).

후처리

  1. temperaturethe reaction mixture was warmed slowly to 0° C.
  2. stirringto room temperature and stirred overnight
  3. washThe organic phase was washed (water, brine)
  4. customseparated
  5. dry with materialdried (Na2SO4)
  6. extractionThe aqueous layer was extracted with EtOAc (twice)
  7. customThe organic layer was separated
  8. washwashed (water, brine)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customto give a yellow oil

출처 및 근거

ORD 기록
ord-f81fd202eadd48cf86367a74f3943e2c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906908B2

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