Sodium Hydroxide → HCID 59497290, compound

HRID 1747301Notes

Reaction equation

HRID 1747301 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[N:9]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[C:8]1=[O:29])C.[OH-].[Na+]>CO>[C:16]([C:13]1[CH:14]=[CH:15][C:10]2[N:9]([CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)[C:8](=[O:29])[N:7]([CH2:6][CH2:5][C:4]([OH:30])=[O:3])[C:11]=2[CH:12]=1)#[N:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59497422HCID 59497422, compound

Product 1

HCID 59497290HCID 59497290, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(6-Cyano-3-naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid ethyl ester (20 mg, 0.05 mmol) in MeOH (5 mL) was added 2N NaOH (3 mL). The reaction mixture was stirred at room temperature for 16 h. When all the starting material was consumed, the reaction mixture was acidified with 1N HCl. The reaction mixture was extracted with CH2Cl2 (×2). The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 10:1 CH2Cl2:MeOH as an eluent to afford 4 mg (22%) of the desired product as an off-white solid. LCMS (ESMS): m/z 372.11 (M+H+).

Workup

  1. customWhen all the starting material was consumed
  2. extractionThe reaction mixture was extracted with CH2Cl2 (×2)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-ef0075aca0424c739f5f386921bfafb4
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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