Lithium Hydroxide → (S)-(4-Chloro-phenyl)-[1-(4,6-dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid

HRID 388468Notes

Reaction equation

HRID 388468 reaction equation
C([O:3][C:4](=[O:37])[C@H:5]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[C:22]3[C:23]([CH3:28])=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=3[S:20][N:19]=2)[C:7]1=[O:29])C.[Li+].[OH-]>O1CCOCC1.O>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([C@H:5]([N:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:17][C:18]3[C:22]4[C:23]([CH3:28])=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=4[S:20][N:19]=3)[C:7]2=[O:29])[C:4]([OH:37])=[O:3])=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68726462(S)-(4-Chloro-phenyl)-[1-(4,6-dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid ethyl ester

Product 1

HCID 25191484(S)-(4-Chloro-phenyl)-[1-(4,6-dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-(4-Chloro-phenyl)-[1-(4,6-dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid ethyl ester (50 mg, 0.094 mmol) in 1,4-dioxane (10 mL) and water (1 mL) is added LiOH (6.7 mg, 0.28 mmol) at room temperature. The solution is stirred at the same temperature for 4 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 is collected by filtration to afford the title compound.: LCMS (ESMS): m/z 506.10 (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 is collected by filtration

Sources & evidence

ORD record
ord-ee1bb0de23584682b02a8dbbe05a7b74
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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