Benzimidazole → Benzimidazol-1-yl-acetic acid tert-butyl ester

HRID 1991211Notes

Reaction equation

HRID 1991211 reaction equation
CC(C)([O-])C.[K+].[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1.Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C1COCC1.O1CCOCC1>[C:21]([O:20][C:18](=[O:19])[CH2:17][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 5798BenzimidazoleHCID 79177tert-Butyl bromoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 54431608Benzimidazol-1-yl-acetic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of potassium tert-butoxide (0.6 mmol) in THF (0.6 mL) was added to a solution of 1H-benzoimidazole (71 mg, 0.6 mmol) in dioxane (15 mL) under stirring. tert-Butyl bromoacetate (97 mg, 0.5 mmol) was added to the white suspension and the mixture was stirred overnight at ambient temperature. The solvents were removed in vacuum and the product was purified on a silica gel column using a gradient of ethyl acetate in heptane) to afford benzimidazol-1-yl-acetic acid tert-butyl ester (110 mg, 95%). Mass spectrum (ESI) m/z: 233.0. 1H NMR (400 MHz, MeOD) δ ppm 1.5 (s, 9 H), 5.0 (s, 2 H), 7.3 (m, 2H), 7.4 (d, J=7.1 Hz, 1H), 7.7 (d, J=6.6 Hz, 1H), 8.1 (s, 1H).

Workup

  1. stirringthe mixture was stirred overnight at ambient temperature
  2. customThe solvents were removed in vacuum
  3. customthe product was purified on a silica gel column

Sources & evidence

ORD record
ord-1a35c3075e14470f97a253d7d94c8b48
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

Loading…