Lithium Hydroxide → 1-((4'-(N-(3-methoxyphenyl)-N-methylsulfamoyl)biphenyl-4-yl)methyl)azetidine-3-carboxylic acid

HRID 717662Notes

Reaction equation

HRID 717662 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([S:22](=[O:34])(=[O:33])[N:23]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=4)[CH3:24])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6]1)=[O:4].[Li+].[OH-]>C1COCC1.O>[CH3:32][O:31][C:27]1[CH:26]=[C:25]([N:23]([CH3:24])[S:22]([C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:14]=[CH:15][C:10]([CH2:9][N:7]4[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:8]4)=[CH:11][CH:12]=3)=[CH:21][CH:20]=2)(=[O:33])=[O:34])[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66615063Methyl-1-((4'-(N-(3-methoxyphenyl)-N-methylsulfamoyl)biphenyl-4-yl)methyl)azetidine-3-carboxylate

Product 1

HCID 461996711-((4'-(N-(3-methoxyphenyl)-N-methylsulfamoyl)biphenyl-4-yl)methyl)azetidine-3-carboxylic acidYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product of Step D (0.06 g, 0.13 mmol) in THF (3 ml) a solution of LiOH (0.006 g, 0.25 mmol) in H2O (1 ml) was added at 80° C. The mixture was stirred for 0.5 h and solvents were evaporated to dryness. The residue was purified by FCC(SiO2) to give the title compound (0.0026 g, 43%) as creamy solid. 1H-NMR (CDCl3:CD3OD) 7.58 (s, 4H); 7.58 (d, 2H, J=8 Hz); 7.56 (d, 2H, J=7.23 Hz); 7.49 (d, 2H, J=8.25 Hz); 7.13 (t, 1H, J=8.14 Hz); 6.76 (dd, 1H, J=8.33, 2.05 Hz); 6.68 (t, 1H, J=2.15 Hz); 6.58 (dd, 1H, J=7.94, 1.32 Hz); 4.25 (s, 2H); 4.21-4.02 (m, 4H); 3.70 (s, 3H); 3.38-3.32 (m, 3H); 3.13 (s, 3H).

Workup

  1. customsolvents were evaporated to dryness
  2. customThe residue was purified by FCC(SiO2)

Sources & evidence

ORD record
ord-b1513339d5b44e66881c766378a55904
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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