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

HRID 475433노트

반응식

HRID 475433 반응식
[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]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 866759963-(2-Formylphenyl)benzo[d]isoxazole-6-carboxamide2회

생성물 1

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

시약·촉매·용매 2

HCID 76524Titanium tetraethoxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-237d4b0f7d3148acad56e9d00b467790
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637551B2

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