Lithium Hydroxide → 3-[1-(4,6-Dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid

HRID 388466Notes

Reaction equation

HRID 388466 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH:5]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:19][C:20]2[C:24]3[C:25]([CH3:30])=[CH:26][C:27]([CH3:29])=[CH:28][C:23]=3[S:22][N:21]=2)[C:9]1=[O:31])[CH2:6][CH3:7].[Li+].[OH-]>O1CCOCC1.C1COCC1.O>[CH3:30][C:25]1[C:24]2[C:20]([CH2:19][N:10]3[C:11]4[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:17](=[O:18])[N:8]([CH:5]([CH2:6][CH3:7])[CH2:4][C:3]([OH:32])=[O:2])[C:9]3=[O:31])=[N:21][S:22][C:23]=2[CH:28]=[C:27]([CH3:29])[CH:26]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 687484073-[1-(4,6-Dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester

Product 1

HCID 251910993-[1-(4,6-Dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[1-(4,6-dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester (65 mg, 0.14 mmol) in 1,4-dioxane (10 mL), THF (5 mL) and water (2 mL) is added LiOH (7 mg, 0.29 mmol) at room temperature. The solution is stirred at room temperature for 8 hours. The solution is concentrated and water is added to the residue. The solution is acidified by 12N HCl in an ice-bath. The precipitated solid filtration to afford the title compound.: LCMS (ESMS): m/z 438.09 (M+H+).

Workup

  1. concentrationThe solution is concentrated
  2. additionwater is added to the residue
  3. customThe solution is acidified by 12N HCl in an ice-bath
  4. filtrationThe precipitated solid filtration

Sources & evidence

ORD record
ord-100eb86654404d3a9037fbc631df7248
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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