Benzyl Bromide → Benzyl 4-sulfamoylbutanoate

HRID 421926Notes

Reaction equation

HRID 421926 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[NH2:7][S:8]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])(=[O:10])=[O:9].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.C(Cl)Cl>[NH2:7][S:8]([CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 27733204-sulfamoylbutanoic Acid

Product 1

HCID 66674779Benzyl 4-sulfamoylbutanoateYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Cs2CO3 (0.51 eq) was added to a solution of 4-(aminosulfonyl)butanoic acid (1 M) in DMF. After 1 h, benzyl bromide (1 eq) was introduced and the reaction left to stir overnight before diluting with DCM and filtering. The filtered liquor was concentrated in vacuo, the residue taken up in DCM and washed with saturated aqueous NaHCO3, water and brine, before being dried over Na2SO4, filtered and concentrated in vacuo. Trituration of the residue with Et2O afforded the title compound as a white solid (27%). (ES+) m/z 280 (M+Na)+

Workup

  1. waitthe reaction left
  2. filtrationfiltering
  3. concentrationThe filtered liquor was concentrated in vacuo
  4. washwashed with saturated aqueous NaHCO3, water and brine
  5. dry with materialbefore being dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-560770eaa5e14215ba5bd1325ee9ec4b
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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