Water → Methyl 1-Acetyl-4-(4-hydroxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate

HRID 1264609Notes

Reaction equation

HRID 1264609 reaction equation
[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:6]([C:26]([O:28][CH3:29])=[O:27])[CH2:5]1)(=[O:3])[CH3:2].B(Br)(Br)Br.O>C(Cl)Cl>[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:6]([C:26]([O:28][CH3:29])=[O:27])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 18612735HCID 18612735, compound

Product 1

HCID 18612782Methyl 1-Acetyl-4-(4-hydroxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylateYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0°) solution of 2.0 g (4.78 mmol) of methyl 1-acetyl-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate in 14 ml of CH2Cl2 was added dropwise 143.3 ml (14.3 mmol) of a 1.0 molar solution of BBr3 in CH2Cl2. The mixture was stirred at room temperature for 1.5 hours. Ice and H2O were added to the reaction mixture and the insolubles filtered off. The filtrate was diluted with CH2Cl2 and H2O and the CH2Cl2 layer separated, washed with brine and dried (Na2 SO4) The solvent was removed under vacuum to give 1.5 g of a white foam. The solid was chromatographed on silica gel with hexane-ethyl acetate (1:1) as solvent to give a foam which was dried under vacuum to give 0.52 g of product as a white foam; Anal. Calc'd for C19H20N2O6S: C, 56 4;H, 5.0; N, 6.9; Found: C 55.1; H, 4.7; N, 6.5.

Workup

  1. filtrationthe insolubles filtered off
  2. additionThe filtrate was diluted with CH2Cl2 and H2O
  3. customthe CH2Cl2 layer separated
  4. washwashed with brine
  5. customdried (Na2 SO4) The solvent
  6. customwas removed under vacuum

Sources & evidence

ORD record
ord-0c7d1f8377c640009a5db50746281e83
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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