Dimethylformamide → HCID 68688698, compound

HRID 1160388Notes

Reaction equation

HRID 1160388 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CN(C)C=O.O1CCCC1.[NH2:16][C:17]1[CH:37]=[CH:36][C:20]([O:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]([CH3:35])[C:32]([OH:34])=[O:33])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH3:1][S:2]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([O:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]([CH3:35])[C:32]([OH:34])=[O:33])=[CH:36][CH:37]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 68686632HCID 68686632, compound

Product 1

HCID 68688698HCID 68688698, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

38 mg (0.332 mM) of methanesulfonyl chloride are added to a mixture of 0.25 ml of dimethylformamide and 1.5 ml of tetrahydrofuran in a 15 ml reactor. 100 mg (0.332 mM) of 2-{2-(4-aminophenoxy)ethoxy}phenylpropanoic acid are then added, followed by addition of 0.060 ml (0.74 mM) of pyridine. The reaction medium is then stirred for 48 hours at room temperature. After extraction with ethyl acetate, 20 mg of 2-{2-[4-(methylsulfonylamino)phenoxy]ethoxy}phenyl-propanoic acid are obtained (yield: 16%).

Workup

  1. extractionAfter extraction with ethyl acetate, 20 mg of 2-{2-[4-(methylsulfonylamino)phenoxy]ethoxy}phenyl-propanoic acid
  2. customare obtained (yield: 16%)

Sources & evidence

ORD record
ord-01d3720d2de047079d3311584314d3d8
Source dataset
uspto-grants-2010_10
Patent number
US07816397B2

Reaction notes

Loading…