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

HRID 594352

反応式

HRID 594352 の反応式
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][C:29]([O:31][CH3:32])=[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]([CH3:22])([CH3:21])[CH3:20])=[O:24])[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 750251,1'-Biphenyl, 2-iodo-HCID 86695623Methyl 4-((tert-butylsulfinyl)imino)butanoateHCID 178418339Butyllithium

生成物 1

HCID 69082814Methyl 4-([1,1'-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)butanoate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (1.916 g; 6.84 mmol) in anh. THF (62 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (4.27 ml; 6.84 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 4-((tert-butylsulfinyl)imino)butanoate (1.500 g; 6.84 mmol) in anh. THF (8 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 methyl 4-([1,1′-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)butanoate. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 374.12 g/mol.

後処理

  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)

出典と根拠

ORDレコード
ord-6db920a20b4347d1a27d0853cf2773bc
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

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