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tert-Butylsulfinamide, (S)-(-)- → tert-butyl 3-[2-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]-3-methylphenyl]propanoate

HRID 64426
Notes
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Reaction equation

HRID 64426 reaction equation
[CH:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=O.[CH3:19][C:20]([S@@:23]([NH2:25])=[O:24])([CH3:22])[CH3:21]>C1COCC1.CCO.CCO.CCO.CCO.[Ti]>[C:20]([S@@:23](/[N:25]=[CH:1]/[C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:24])([CH3:22])([CH3:21])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86713435Tert-butyl 3-(2-formyl-3-methylphenyl)propanoate

Product 1

HCID 90072800tert-butyl 3-[2-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]-3-methylphenyl]propanoateYield 77.8%

Reagents, catalysts & solvents 2

HCID 2724286Titanium(IV)ethoxideCatalystHCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 305 mg of tert-butyl 3-(2-formyl-3-methylphenyl)propanoate in 3 ml of THF 3 ml were added 298 mg of (S)-2-methyl-2-propanesulfinamide and 0.62 ml of tetraethyl orthotitanate, followed by stirring at room temperature for 16 hours. The reaction mixture was poured into ice water and the insoluble material was filtered through Celite. To the filtrate was added chloroform to carry out a layer separation operation. The organic layer was washed with water and subsequentially with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 336 mg of tert-butyl 3-{2-[(E)-{[(S)-tert-butylsulfinyl]imino}methyl]-3-methylphenyl}propanoate.

Workup

  1. filtrationthe insoluble material was filtered through Celite
  2. additionTo the filtrate was added chloroform
  3. customa layer separation operation
  4. washThe organic layer was washed with water and subsequentially with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2acaaa5049f34efc927e8517584e58cd
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447090B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes