Ethyl n-[(5-chloro-2-benzimidazolyl)methyl]-n-(4-chlorophenyl)glycinate → n-[(5-Chloro-2-benzimidazolyl)methyl]-n-(4-chlorophenyl)glycine
Reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([CH2:9][N:10]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:11][C:12]([O:14]CC)=[O:13])[NH:8][C:4]=2[CH:3]=1>CO.O>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([CH2:9][N:10]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:11][C:12]([OH:14])=[O:13])[NH:8][C:4]=2[CH:3]=1Participants
4
Procedure
Ethyl N-[(5-chloro-2-benzimidazolyl)methyl]-N-(4-chlorophenyl)glycinate (0.15 g) was dissolved in methanol (3 ml). A solution of LiOH monohydrate (92 mg) in water (0.5 ml) was added and the cloudy mixture was stirred at rt for 2 h. Water (25 ml) was added and the aqueous layer was washed with EtOAc (20 ml) and diethyl ether (20 ml). By addition of 1M HCl a pH of 5 was adjusted. The white precipitate was extracted with EtOAc (4×50 ml). The combined organic layers were dried (sodium sulfate) and concentrated to give a yellowish solid which was further purified by trituration with acetone to provide N-[(5-chloro-2-benzimidazolyl)methyl]-N-(4-chlorophenyl)glycine (43 mg) as colourless crystals.
Workup
- washthe aqueous layer was washed with EtOAc (20 ml) and diethyl ether (20 ml)
- additionBy addition of 1M HCl a pH of 5
- extractionThe white precipitate was extracted with EtOAc (4×50 ml)
- dry with materialThe combined organic layers were dried (sodium sulfate)
- concentrationconcentrated
- customto give a yellowish solid which
- customwas further purified by trituration with acetone
Sources & evidence
- ORD record
- ord-3e0496765b454761a0581588e2d78053
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912186B2
Reaction notes
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