Ammonium Chloride → methyl 3-[(1S)-1-{[(S)-tert-butylsulfinyl]amino}propyl]benzoate

HRID 64450

반응식

HRID 64450 반응식
[C:1]([S@@:5](/[N:7]=[CH:8]/[C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH2:19]([Zn]CC)[CH3:20].CCCCCC.C([Mg]Br)C.C(OCC)C.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:1]([S@@:5]([NH:7][C@H:8]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])[CH2:19][CH3:20])=[O:6])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 90072367methyl 3-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]benzoateHCID 178443585HCID 178443585, 화합물HCID 178467792HCID 178467792, 화합물

생성물 1

HCID 86713465methyl 3-[(1S)-1-{[(S)-tert-butylsulfinyl]amino}propyl]benzoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 500 mg of methyl 3-[(E)-{[(S)-tert-butylsulfinyl]imino}methyl]benzoate in 12 ml of THF was added 0.50 ml of a 1 M diethylzinc/hexane solution at −78° C., followed by stirring at the same temperature for 5 minutes. 0.80 ml of a 3 M ethylmagnesium bromide/diethyl ether solution was added thereto at −78° C., followed by stirring at the same temperature for 2 hours. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 447 mg of methyl 3-[(1S)-1-{[(S)-tert-butylsulfinyl]amino}propyl]benzoate.

후처리

  1. customat −78° C.
  2. stirringby stirring at the same temperature for 2 hours
  3. customa layer separation operation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bfc183d973b3464fa90f16ef138d3c7f
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447090B2

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