Ammonium Chloride → Methyl 4-(2,6-dimethoxyphenyl)-4-(1,1-dimethylethylsulfinamido)butanoate

HRID 594335

反応式

HRID 594335 の反応式
I[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][CH3:11].[Li]CCCC.[C:17]([S:21]([N:23]=[CH:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[O:22])([CH3:20])([CH3:19])[CH3:18].[NH4+].[Cl-]>C1COCC1.O.CCOCC>[CH3:11][O:10][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[CH:24]([NH:23][S:21]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:22])[CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 113914072-Iodo-1,3-dimethoxybenzeneHCID 86695623Methyl 4-((tert-butylsulfinyl)imino)butanoateHCID 178418339Butyllithium

生成物 1

HCID 69084999Methyl 4-(2,6-dimethoxyphenyl)-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.) yellow solution of 2-iodo-1,3-dimethoxybenzene (13.798 g; 52.25 mmol) in anh. THF (200 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (32.66 ml; 52.25 mmol). The resulting slightly yellow solution was further stirred at −78° C. for 15 min. A yellow solution of methyl 4-((tert-butylsulfinyl)imino)butanoate (7.640 g; 34.83 mmol) in anh. THF (50 ml) was then added dropwise to the cooled reaction mixture, and stirring at −78° C. was continued for 45 min. The resulting yellow reaction mixture was treated successively with aq. sat. NH4Cl (20 ml), Et2O (250 ml) and water (75 ml). The separated yellow 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=30/1) afforded methyl 4-(2,6-dimethoxyphenyl)-4-(1,1-dimethylethylsulfinamido)butanoate as a yellow oil. LC-MS (conditions A): tR=0.73 min.; [M+H]+: 358.34 g/mol.

後処理

  1. stirringstirring at −78° C.
  2. waitwas continued for 45 min
  3. washThe separated yellow organic layer was then washed with brine (75 ml)
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH=30/1)

出典と根拠

ORDレコード
ord-04766bfd9ee44fe5856bf62b372a1cc9
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

関連ノート

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