Diisopropylcarbodiimide → (4-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}benzylcarbamoyl)methanesulfonic Acid

HRID 347792

Reaction equation

HRID 347792 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:11](=[O:20])[CH:10]2[CH2:21][CH2:22][CH:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[OH:24])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[S:41]([CH2:45][C:46](O)=[O:47])([OH:44])(=[O:43])=[O:42].C(N=C=NC(C)C)(C)C.OC1C2N=NNC=2C=CC=1>CN(C)C=O>[F:19][C:16]1[CH:15]=[CH:14][C:13]([N:12]2[C:11](=[O:20])[CH:10]([CH2:21][CH2:22][CH:23]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[OH:24])[CH:9]2[C:6]2[CH:7]=[CH:8][C:3]([CH2:2][NH:1][C:46]([CH2:45][S:41]([OH:44])(=[O:43])=[O:42])=[O:47])=[CH:4][CH:5]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 12734DiisopropylcarbodiimideHCID 31257Sulfoacetic acidHCID 81531DiisopropylethylamineHCID 222520324-(4-Aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-oneHCID 178418300HCID 178418300, compound

Product 1

HCID 21083138(4-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}benzylcarbamoyl)methanesulfonic Acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 120 mg of 4-(4-aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one (17), and 48 μl of diisopropylethylamine in 1 ml of dimethylformamide was added to a solution of 40 mg of sulfoacetic acid, 110 μl of diisopropylcarbodiimide, and 76 mg of hydroxybenzotriazole in 2 ml of dimethylformamide, and the mixture was stirred at room temperature for 12 h. The reaction solution was concentrated and separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20->10/90). This gave the product of molecular weight 544.58 (C27H26F2N2O6S1); MS (ESI) 527.10 (M+H+—H2O)

Workup

  1. concentrationThe reaction solution was concentrated
  2. customseparated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20->10/90)
  3. customThis gave the product of molecular weight 544.58 (C27H26F2N2O6S1)

Sources & evidence

ORD record
ord-3e2da4d0ec654069983200b41eadd3b8
Source dataset
uspto-grants-2007_02
Patent number
US07176193B2

Linked notes

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