Methanol → HCID 59497689, compound

HRID 1747317Notes

Reaction equation

HRID 1747317 reaction equation
[C:1]1([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13]2=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:22]([O:26][CH3:27])(=[O:25])[CH:23]=[CH2:24].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.CO.[NH4+].[Cl-]>CN(C=O)C.O>[CH3:27][O:26][C:22](=[O:25])[CH2:23][CH2:24][N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:13]1=[O:21]

Participants

8

Reactant 5

HCID 887MethanolHCID 7294Methyl AcrylateHCID 25517Ammonium ChlorideHCID 66854Benzyltrimethylammonium hydroxideHCID 24071726HCID 24071726, compound

Product 1

HCID 59497689HCID 59497689, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-naphthalen-1-ylmethyl-1,3-dihydro-benzimidazol-2-one (200 mg, 0.73 mmol) in DMF (3.0 mL) are added methyl acrylate (0.07 mL, 0.8 mmol) and 40% benzyltrimethyl ammonium hydroxide in MeOH (0.03 mL, 0.073 mmol). The resulting mixture is stirred at room temperature for 1.5 h and then Sat. NH4Cl (5 mL) and water (20 mL) are added. The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined, washed with water (3×75 dried over MgSO4 and concentrated to give crude product. Purification by flash column chromatography using 30% EtOAc in Hexanes affords 220 mg (84%) of 3-(3-naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×50 mL)
  2. washwashed with water (3×75
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give crude product
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-3555873038324149b1ee54ba327e3046
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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