Potassium Carbonate → Methyl 2-(N-(4-ethoxy-4-oxobutyl)-4-methylphenylsulfonamido)benzoate

HRID 220776Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: 80 °C

Procedure

2-(Toluene-4-sulfonylamino)-benzoic acid methyl ester from Example E5.1 (100 g) was dissolved in DMF (250 ml). Potassium carbonate (125 g) and ethyl 4-bromobutanoate (60 g) were added and the mixture was heated at 80° C. for 18 h. The mixture was cooled to room temperature, filtered and reduced in vacuo. The residue was partitioned between chloroform and 1M HCl solution. The aqueous layer was extracted with chloroform. The organic layers were combined, washed with brine, dried, filtered and concentrated in vacuo. The material was crystallised from EtOAc/hexane and dried in a vacuum oven at 60° C. for 3 hours to yield the title compound (98.6 g, 72%).

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered
customThe residue was partitioned between chloroform and 1M HCl solution
extractionThe aqueous layer was extracted with chloroform
washwashed with brine
customdried
filtrationfiltered
concentrationconcentrated in vacuo
customThe material was crystallised from EtOAc/hexane
customdried in a vacuum oven at 60° C. for 3 hours

Sources & evidence

ORD record: ord-551effd129c34cff99f617c04d0d59be
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

Loading…