Water → HCID 25125211, compound

HRID 1747457Notes

Reaction equation

HRID 1747457 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([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:11]1=[O:31])[CH2:7][CH2:8][CH3:9])C.O.[Li+].[OH-]>O1CCOCC1>[CH3:30][C:25]1[C:24]2[C:20]([CH2:19][N:12]3[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:32])=[O:3])[C:11]3=[O:31])=[N:21][S:22][C:23]=2[CH:28]=[C:27]([CH3:29])[CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59497241HCID 59497241, compound

Product 1

HCID 25125211HCID 25125211, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of product 3-[3-(4,6-Dimethyl-1,2-benzisothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (23 mg, 0.051 mmol)) in 1,4-dioxane (5 mL) and water (1 mL) was added LiOH (2.4 mg, 0.1 mmol) at room temperature. The solution was stirred at the same temperature for 4 hours. The solution was concentrated and water was added to the residue. The solution was acidified by 12N HCl in an ice-bath. The solid that preciptate out from the solution was collected by filtration. The solid was dried under vacuum and was confirmed to be the desirable product (10 mg, 46%). LCMS (ESMS): m/z 424.18 (M+H+).

Workup

  1. concentrationThe solution was concentrated
  2. additionwater was added to the residue
  3. customThe solution was acidified by 12N HCl in an ice-bath
  4. filtrationThe solid that preciptate out from the solution was collected by filtration
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-d03c26ff25844667b6cc914a74088e5a
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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