Ethyl Acetate → 3-[2-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]phenyl]-1,2-benzoxazole-6-carboxamide

HRID 475433ノート

反応式

HRID 475433 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]([NH2:20])=[O:19])=[CH:17][C:12]=2[O:11][N:10]=1)=O.[C:21]([S@@:25]([NH2:27])=[O:26])([CH3:24])([CH3:23])[CH3:22].C(OCC)(=O)C>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:21]([S@@:25](/[N:27]=[CH:1]/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]([NH2:20])=[O:19])=[CH:17][C:12]=2[O:11][N:10]=1)=[O:26])([CH3:24])([CH3:23])[CH3:22]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 866759963-(2-Formylphenyl)benzo[d]isoxazole-6-carboxamide2 回

生成物 1

HCID 889827103-[2-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]phenyl]-1,2-benzoxazole-6-carboxamide収率 99.7%

試薬・触媒・溶媒 2

HCID 76524Titanium tetraethoxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 3-(2-formylphenyl)benzo[d]isoxazole-6-carboxamide (Compound 7) (4.12 g) in tetrahydrofuran (50 mL) was added (S)-(−)-t-butylsulfinamide (1.97 g) followed by titanium (IV) ethoxide (4.8 mL). The mixture was stirred for three days then poured onto stirred ice-water (200 mL) and ethyl acetate (200 mL) added and filtered through dicalite and the plug of solid was washed with hot ethyl acetate (200 mL), the organic layer was dried over anhydrous magnesium sulfate and evaporated to give the title compound (5.7 g) as a partially solidified gum.

後処理

  1. additionthen poured
  2. additionadded
  3. filtrationfiltered through dicalite
  4. washthe plug of solid was washed with hot ethyl acetate (200 mL)
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-237d4b0f7d3148acad56e9d00b467790
出典データセット
uspto-grants-2014_01
特許番号
US08637551B2

反応ノート

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