Ammonium Chloride → Ethyl 4-([1,1'-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)-2-methylbutanoate

HRID 594354노트

반응식

HRID 594354 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][CH:28]([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[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]([CH3:21])([CH3:20])[CH3:22])=[O:24])[CH2:27][CH:28]([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 750251,1'-Biphenyl, 2-iodo-HCID 86695624Ethyl 4-((tert-butylsulfinyl)imino)-2-methylbutanoateHCID 178418339Butyllithium

생성물 1

HCID 86695627Ethyl 4-([1,1'-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)-2-methylbutanoate

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (680 mg; 2.43 mmol) in anh. THF (20 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.52 ml; 2.43 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of ethyl 4-((tert-butylsulfinyl)imino)-2-methylbutanoate (600 mg; 2.43 mmol) in anh. THF (5 ml) was added to the cooled reaction mixture, and stirring was continued from −78° C. to 0° C. over 1 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (80 ml), Et2O (250 ml) and water (75 ml). The separated organic layer was then washed with brine (75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded ethyl 4-([1,1′-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)-2-methylbutanoate as a mixture of stereoisomers. LC-MS (conditions A): tR=0.93 min.; [M+H]+: 401.79 g/mol and tR=0.94 min.; [M+H]+: 401.80 g/mol.

후처리

  1. stirringstirring
  2. waitwas continued from −78° C. to 0° C. over 1 h
  3. customThe resulting reaction mixture
  4. washThe separated organic layer was then washed with brine (75 ml)
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM/MeOH=25/1)

출처 및 근거

ORD 기록
ord-0c7c69b30ca541d0b2616f5e0b8a8fda
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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