tert-Butyl 2-(methoxy(methyl)amino)-1-methyl-2-oxoethylcarbamate → (S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate

HRID 473442

반응식

HRID 473442 반응식
CON(C)[C:4](=[O:15])[CH:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].C(=O)=O.C(#N)C.C([Mg]Cl)(C)C.Br[Mg][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1>C1COCC1>[O:15]=[C:4]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH3:6]

참가 물질

6

반응물 4

HCID 375613tert-Butyl 2-(methoxy(methyl)amino)-1-methyl-2-oxoethylcarbamateHCID 86587134Acetonitrile dry iceHCID 178418918HCID 178418918, 화합물HCID 178419667HCID 178419667, 화합물

생성물 1

HCID 58318617(S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

tert-Butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (50.0 g, 215 mmol) in THF (450 mL) was cooled to −40° C. (dry ice/acetonitrile) and slowly charged with isopropylmagnesium chloride (2.0M, 102.2 mL, 0.95 eq). After a clear solution was obtained (became clear at −20° C. and milky again at −40° C.), bromo(pyridin-2-ylmethyl)magnesium solution (see below for preparation) was added drop wise using cannula before warming to rt overnight. The reaction mixture was quenched with NH4Cl solution and extracted with EtOAc (500 mL×2). The combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated under high vacuum to give (S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate as a tan oil. Small scale reaction was purified by combiflash (EtOAc/hexane, up to 1/3) to give a red oil. Mass Spectrum (ESI) m/e=265 (M+1).

후처리

  1. customAfter a clear solution was obtained (
  2. custombecame clear at −20° C.
  3. customThe reaction mixture was quenched with NH4Cl solution
  4. extractionextracted with EtOAc (500 mL×2)
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under high vacuum

출처 및 근거

ORD 기록
ord-6dfe5724be4149c79381fa186e91e7bf
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633313B2

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