N-Methyltaurine → 2-{[4-(4-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenoxy)butyl]methylamino}ethanesulfonic acid

HRID 2104931Notes

Reaction equation

HRID 2104931 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22]I)=[CH:14][CH:13]=3)[CH:10]([CH2:24][CH2:25][CH:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[OH:27])[C:9]2=[O:35])=[CH:4][CH:3]=1.[CH3:36][NH:37][CH2:38][CH2:39][S:40]([OH:43])(=[O:42])=[O:41].C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:35])[CH:10]([CH2:24][CH2:25][CH:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[OH:27])[CH:11]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:37]([CH3:36])[CH2:38][CH2:39][S:40]([OH:43])(=[O:42])=[O:41])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7882N-MethyltaurineHCID 11430Potassium CarbonateHCID 222520481-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-hydroxypropyl]-4-[4-(4-iodobutoxy)phenyl]azetidin-2-one

Product 1

HCID 235935122-{[4-(4-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenoxy)butyl]methylamino}ethanesulfonic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

64.5 mg of 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(4 iodobutoxy)phenyl]azetidin-2-one are dissolved in 3 ml of methanol. 60.7 mg of 2-methylaminoethanesulfonic acid are then dissolved in 1 ml of water, and 30.4 mg of potassium carbonate are added. The reaction solution is stirred at 50° C. for 8 h. After concentration using a rotary evaporator at 40° C., the residue is passed over a reverse-phase cartridge (methanol). The resulting crude product is dissolved in hot methanol. The precipitate formed on cooling is filtered off, and the mother liquor is concentrated using a rotary evaporator. The product is obtained as an oil.

Workup

  1. concentrationAfter concentration
  2. customa rotary evaporator at 40° C.
  3. dissolutionThe resulting crude product is dissolved in hot methanol
  4. customThe precipitate formed
  5. temperatureon cooling
  6. filtrationis filtered off
  7. concentrationthe mother liquor is concentrated
  8. customa rotary evaporator
  9. customThe product is obtained as an oil

Sources & evidence

ORD record
ord-3dcc3ea68e2649379e684e752079b19d
Source dataset
uspto-grants-2009_08
Patent number
US07576200B2

Reaction notes

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