N-Methyltaurine → 2-[(4-{4-[3-[3-(4-Fluorophenyl)-3-hydroxypropyl]-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenoxy}butyl)methylamino]ethylsulfonic Acid

HRID 132748Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:36])[CH2:9][CH2:10][CH:11]2[CH:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:13]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33]F)=[CH:25][CH:24]=3)[C:12]2=[O:35])=[CH:4][CH:3]=1.[CH3:37][NH:38][CH2:39][CH2:40][S:41]([OH:44])(=[O:43])=[O:42].C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:36])[CH2:9][CH2:10][CH:11]2[C:12](=[O:35])[N:13]([C:23]3[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][N:38]([CH3:37])[CH2:39][CH2:40][S:41]([OH:44])(=[O:43])=[O:42])=[CH:27][CH:28]=3)[CH:14]2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

130 mg of 3-[3-(4-fluorophenyl)-3-hydroxypropyl]-1-[4-(4-fluorobutoxy)phenyl]-4-(4-methoxyphenyl)azetidin-2-one (7) were dissolved in 6 ml of absolute methanol. 120 mg of N-methyltaurine in 2 ml of water and 60 mg of potassium carbonate were then added. The mixture was stirred at 50° C. for 24 h. The reaction mixture was concentrated using a rotary evaporator and the residue was purified by preparative chromatography. Freeze-drying gave the product (50 mg) as an oil.

Workup

concentrationThe reaction mixture was concentrated
customa rotary evaporator
customthe residue was purified by preparative chromatography
customFreeze-drying

Sources & evidence

ORD record: ord-ad9c5af0208545b484ff31c9005b8bfb
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07388004B2

Reaction notes

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