Benzyl Bromide → HCID 58743870, compound

HRID 723315Notes

Reaction equation

HRID 723315 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][S:21]([CH2:24]Cl)(=[O:23])=[O:22])[C:15]=2[OH:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[O:26][CH2:24][S:21](=[O:23])(=[O:22])[N:20]([CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:16]=3[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium Carbonate2×HCID 58743868HCID 58743868, compound

Product 1

HCID 58743870HCID 58743870, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask containing 7 mL methanol was added 4-(3-chloromethanesulfonylamino-2-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (190 mg., 0.471 mmol) and potassium carbonate (195 mg, 1.4 mmol). The suspension was refluxed for two hours under nitrogen and allowed to cool to room temperature. To the reaction mixture was added benzyl bromide (0.083 mL, 0.7 mmol) and potassium carbonate (87 mg., 0.7 mmol), and the reaction was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vacuo and the resulting crude solid was dissolved in ethyl acetate. The solution was washed with 50 mL water and 50 mL brine, and the ethyl acetate was removed in vacuo. The resulting residue was purified by flash chromatography to give 57 mg of 4-(1-Benzyl-2,2-dioxo-2,3-dihydro-1H-benzo[4,2,1]oxathiazin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester as a light purple oil (26%). (M+H)+=460

Workup

  1. temperatureThe suspension was refluxed for two hours under nitrogen
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe resulting crude solid was dissolved in ethyl acetate
  4. washThe solution was washed with 50 mL water and 50 mL brine
  5. customthe ethyl acetate was removed in vacuo
  6. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-20f55dafa44240d392f340332d8ad337
Source dataset
uspto-grants-2006_11
Patent number
US07141562B2

Reaction notes

Loading…