tert-Butylsulfinamide, (S)-(-)- → (S)-ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-(tert-butylsulfinylimino)acetate

HRID 931555

反応式

HRID 931555 の反応式
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[I-].C([Zn+])C(C)(C)C.[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:29][CH2:30][O:31][CH3:32])=[C:20]([C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:21]=1>>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:29][CH2:30][O:31][CH3:32])=[C:20]([C:22](=[N:7][S@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:21]=1

参加物

4

反応物 3

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 57475646Ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-oxoacetateHCID 178445888HCID 178445888、化合物

生成物 1

HCID 86658358(S)-ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-(tert-butylsulfinylimino)acetate収率 51%

実験手順

A flask was charged with (S)-2-methylpropane-2-sulfinamide (0.764 g, 6.31 mmol) and neopentylzinc(II) iodide (0.5 M in THF, 10.0 mL, 5.00 mmol) was added under nitrogen atmosphere. The mixture was stirred at RT for 15 minutes and ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-oxoacetate (1.00 g, 3.15 mmol) was added in one portion. The reaction mixture was quenched with saturated aqueous ammonium chloride after 8 h. The reaction was partitioned between EtOAc and water. The organic phase was separated, washed with NH4Cl, water and brine. The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel chromatography (10-30% EtOAc/hexane) to provide 0.675 g (S)-ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-(tert-butylsulfinylimino)acetate.

後処理

  1. additionwas added under nitrogen atmosphere
  2. customThe reaction mixture was quenched with saturated aqueous ammonium chloride after 8 h
  3. customThe reaction was partitioned between EtOAc and water
  4. customThe organic phase was separated
  5. washwashed with NH4Cl, water and brine
  6. dry with materialThe organic phase was dried over MgSO4
  7. customthe solvent was removed under reduced pressure
  8. customThe crude material was purified by silica gel chromatography (10-30% EtOAc/hexane)

出典と根拠

ORDレコード
ord-c0374a2d06684bd39f54daca3f787e62
出典データセット
uspto-grants-2016_03
特許番号
US09296759B2

関連ノート

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