Hydrochloric Acid → HCID 56666721, compound

HRID 1747318Notes

Reaction equation

HRID 1747318 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:30])[CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([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:10]1=[O:29].Cl>O.CO>[C:19]1([CH2:18][N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:9]([CH2:8][CH2:7][C:6]([OH:30])=[O:5])[C:10]2=[O:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59497689HCID 59497689, compound

Product 1

HCID 56666721HCID 56666721, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Lithium hydroxide monohydrate (31 mg, 0.75 mmol) is dissolved in water (3.5 mL) and this solution is added into 3-(3-naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester (180 mg, 0.5 mmol) in methanol (3.5 mL) at room temperature. The mixture is stirred for 6 hr and 1.0 M HCl aqueous solution (1.5 mL) is added along with water (25 mL). Then the mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined, dried over MgSO4 and concentrated to give 170 mg of crude 3-(3-Naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid which is used in the following step without further purification.

Workup

  1. extractionThen the mixture is extracted with EtOAc (3×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aa9d891015c8441db1fe656c2b8be0c1
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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