Ammonium Chloride → Methyl 5-([1,1'-biphenyl]-2-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate

HRID 594350

반응식

HRID 594350 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li]CCCC.[C:19]([S:23]([N:25]=[CH:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[O:24])([CH3:22])([CH3:21])[CH3:20].[NH4+].[Cl-]>C1COCC1.O.CCOCC>[C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:26]([NH:25][S:23]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:24])[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 750251,1'-Biphenyl, 2-iodo-HCID 74336636Methyl 5-((tert-butylsulfinyl)imino)pentanoateHCID 178418339Butyllithium

생성물 1

HCID 69081687Methyl 5-([1,1'-biphenyl]-2-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (617 mg; 2.20 mmol) in anh. THF (5 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.50 ml; 2.40 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 5-((tert-butylsulfinyl)imino)pentanoate (514 mg; 2.20 mmol) in anh. THF (2 ml) was added to the cooled reaction mixture, and stirring at −78° C. was continued for 10 min., and then at −20° C. for 2 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (15 ml), Et2O (30 ml) and water (15 ml). The separated organic layer was then washed with brine (15 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=7/3) afforded methyl 5-([1,1′-biphenyl]-2-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate as a yellow oil. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 387.83 g/mol.

후처리

  1. stirringstirring at −78° C.
  2. waitwas continued for 10 min.
  3. waitat −20° C. for 2 h
  4. customThe resulting reaction mixture
  5. washThe separated organic layer was then washed with brine (15 ml)
  6. dry with materialdried over anh. MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customPurification by FC (heptane/AcOEt=7/3)

출처 및 근거

ORD 기록
ord-cee37a7fb1ac483c9bb64648e3d802e4
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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