Benzyl Bromide → HCID 11668811, compound

HRID 1373742Notes

Reaction equation

HRID 1373742 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O.C(Cl)Cl>CN(C)C=O>[CH2:22]([N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:9])=[O:10])[C@H:12]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:13]([NH2:15])=[O:14])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21908982Water methylene chlorideHCID 51536914HCID 51536914, compound

Product 1

HCID 11668811HCID 11668811, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-2-(4-chloro-benzenesulfonylamino)-2-phenyl-acetamide (350 mg, 1.1 mmol) in 4 mL of dimethylformamide are added benzylbromide (0.18 mL, 1.1 mmol) and potassium carbonate (179 mg, 1.3 mmol). The reaction is heated overnight at 50° C., poured into water/methylene chloride and extracted with methylene chloride. The combined organics are dried with sodium sulfate, concentrated in vacuo, and the resultant residue purified on silica gel chromatography to provide the title compound. C13 NMR (100 MHz, CDCl3) 50.3, 64.8, 127.6, 128.4, 128.6, 129.0, 129.1, 129.3, 129.4, 130.2, 133.9, 136.8, 138.6, 139.4, 171.7. MS 415.1 m/z (M+1).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organics are dried with sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe resultant residue purified on silica gel chromatography

Sources & evidence

ORD record
ord-9345c54144694249b0c1ff9f15671422
Source dataset
uspto-grants-2007_01
Patent number
US07163942B2

Reaction notes

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