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

HRID 475433Notes

Reaction equation

HRID 475433 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-237d4b0f7d3148acad56e9d00b467790
Source dataset
uspto-grants-2014_01
Patent number
US08637551B2

Reaction notes

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