Benzophenone imine → HCID 57827439, compound

HRID 1842271Notes

Reaction equation

HRID 1842271 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].[C:67]([O:71][C:72]([N:74]([C:82]1[S:83][C@@H:84]2[CH2:90][O:89][CH2:88][CH2:87][C@:85]2([C:91]2[CH:96]=[CH:95][CH:94]=[C:93](Br)[CH:92]=2)[N:86]=1)C(OC(C)(C)C)=O)=[O:73])([CH3:70])([CH3:69])[CH3:68]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:1](=[N:14][C:93]1[CH:92]=[C:91]([C@:85]23[CH2:87][CH2:88][O:89][CH2:90][C@H:84]2[S:83][C:82]([NH:74][C:72](=[O:73])[O:71][C:67]([CH3:69])([CH3:68])[CH3:70])=[N:86]3)[CH:96]=[CH:95][CH:94]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 57827764HCID 57827764, compound

Product 1

HCID 57827439HCID 57827439, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

Benzophenone imine (244 μL), BINAP (60.6 mg), tris(dibenzylideneacetone)dipalladium (0) (44.6 mg) and sodium tert-butoxide (233 mg) were added to a solution of (±)-N,N-bis(tert-butoxycarbonyl) [(3aS*,7aR*)-7a-(3-bromophenyl)-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]thiazol-2-yl]amine (250 mg) in toluene (20 mL). After replacement with nitrogen, the mixture was stirred at 85° C. for four hours. The reaction solution was returned to room temperature, and water was added to the reaction mixture. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (165 mg).

Workup

  1. customwas returned to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-81bb21faa8364775958838f3ba1fd3ab
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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