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Ammonium Chloride → (NE,R)-N-[2-[tert-butyl(dimethyl)silyl]oxy-1-(3-fluorophenyl)ethylidene]-2-methylpropane-2-sulfinamide

HRID 1051355
Notes
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Reaction equation

HRID 1051355 reaction equation
[Si:1]([O:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:19][C:20]([S@:23]([NH2:25])=[O:24])([CH3:22])[CH3:21].[NH4+].[Cl-]>C1COCC1>[Si:1]([O:8][CH2:9]/[C:10](=[N:25]/[S@@:23]([C:20]([CH3:22])([CH3:21])[CH3:19])=[O:24])/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 867119952-(Tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)ethanone

Product 1

HCID 89998706(NE,R)-N-[2-[tert-butyl(dimethyl)silyl]oxy-1-(3-fluorophenyl)ethylidene]-2-methylpropane-2-sulfinamideYield 49%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a mixture of 58a (11.3 g, 42.1 mmol) and (R)-2-methylpropane-2-sulfinamide (6.60 g, 54.7 mmol) in THF (200 mL) at RT was added Ti(Oi-Pr)4 (29.9 g, 105 mmol). The reaction mixture was heated to reflux under N2 overnight. The mixture was cooled then treated with saturated NH4Cl (5.0 mL), and the insoluble material was filtered. The filtrate was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc gradient (60:1 to 20:1) to afford 7.6 g (49%) of (R,E)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide (58b) as yellow oil. LCMS (ESI) m/z: 372.2 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under N2 overnight
  3. temperatureThe mixture was cooled
  4. filtrationthe insoluble material was filtered
  5. dry with materialThe filtrate was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with petroleum ether/EtOAc gradient (60:1 to 20:1)

Sources & evidence

ORD record
ord-c83d58cb684a41f599fe22013f2c2183
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09388171B2

Reaction notes

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