Sodium Hydroxide → Tert-butyl (2-oxo-2,3-dihydrobenzimidazol-1-yl)acetate

HRID 896317Notes

Reaction equation

HRID 896317 reaction equation
C(O[C:4]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15])=O)C.CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C.[C:37]([O:41][C:42](=[O:45])CBr)([CH3:40])([CH3:39])[CH3:38].[OH-].[Na+]>C1COCC1.CCOCC>[C:37]([O:41][C:42](=[O:45])[CH2:4][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15])([CH3:40])([CH3:39])[CH3:38]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylateHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphorane

Product 1

HCID 20814117Tert-butyl (2-oxo-2,3-dihydrobenzimidazol-1-yl)acetateYield 50.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid ethyl ester (3 g, 14.78 mmol) (N. Meanwell et al, J. Org. Chem, 1995, 60(6), 1565-82) in THF (100 ml) was treated with BTPP(5.4 ml, 17.74 mmol) followed by t-butylbromoacetate (2.4 ml, 16.3 mmol) and the mixture was stirred for 30 minutes. The solution was diluted with ether and washed with water, dired over MgSO4 and concentrated. The residue was dissolved in MeOH (30 ml) and treated with NaOH (10 N, 3 ml, 30 mmol) and stirred for 1 h at 23° C. The solvent was removed and the residue diluted with ether and washed with 1N HCl, saturated NaCl dried over MgSO4 and concentrated. The residue was purified by flash chromatography to give 1.84 g (50%) (2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid tert-butyl ester as a white solid.

Workup

  1. washwashed with water
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in MeOH (30 ml)
  4. stirringstirred for 1 h at 23° C
  5. customThe solvent was removed
  6. additionthe residue diluted with ether
  7. washwashed with 1N HCl, saturated NaCl
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-dea6c48ecad14beb983c1c511e4687d1
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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