Ethyl Acetate → HCID 46837646, compound

HRID 1399555Notes

Reaction equation

HRID 1399555 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 46837646HCID 46837646, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f81fd202eadd48cf86367a74f3943e2c
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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