Boron tribromide → HCID 18612951, compound

HRID 1264610Notes

Reaction equation

HRID 1264610 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]([C:23]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)=[O:24])[CH2:14][CH:13]2[C:30]([O:32][CH3:33])=[O:31])(=[O:11])=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]([C:23]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)=[O:24])[CH2:14][CH:13]2[C:30]([O:32][CH3:33])=[O:31])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18612833HCID 18612833, compound

Product 1

HCID 18612951HCID 18612951, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 4.0 g (8.22 mmol) of methyl 4-(4-methoxybenzenesulfonyl)-1-(2-thienylcarbonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate ml of CH2Cl2 chilled to 0° C., was added slowly 16.4 ml (16.44 mmol) of 1.0 molar solution of boron tribromide in CH2Cl2. The mixture was stirred at room temperature overnight and diluted with CH2Cl2. The mixture was filtered and the solid washed with CHCl2. and H2O. The filtrate was diluted with H2O and the organic layer separated. The solvent was removed under vacuum and the solid chromatographed on silica gel with hexane-ethyl acetate (1:1) as solvent to give 0.80 g of off white foam; Mass Spectrum (ES) 473.5 (M+H); Anal. Calc'd for C22H20N2O6S2: C, 55.9; H, 4.3; N, 5.9. Found: C, 54.5; H, 4.4; N, 5.5.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid washed with CHCl2
  3. additionThe filtrate was diluted with H2O
  4. customthe organic layer separated
  5. customThe solvent was removed under vacuum
  6. customthe solid chromatographed on silica gel with hexane-ethyl acetate (1:1) as solvent
  7. customto give 0.80 g of off white foam

Sources & evidence

ORD record
ord-329be43d0c78435e83c62155e5b27692
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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