Sodium Hydroxide → 2-(3-(4-Benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyric acid
Reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]2[CH2:18][CH2:17][N:16]([CH:19]([CH:25]([CH3:27])[CH3:26])[C:20]([O:22]CC)=[O:21])[C:15]2=[O:28])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]2[CH2:18][CH2:17][N:16]([CH:19]([CH:25]([CH3:27])[CH3:26])[C:20]([OH:22])=[O:21])[C:15]2=[O:28])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
Ethyl 2-(3-(4-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (0.330 g; 0.80 mmol) was dissolved in methanol (MeOH; 6 ml). NaOH solution (1N; 3 ml) as added, and the mixture was stirred at RT for 3 h. The solvent was removed under reduced pressure, and saturated NaH2PO4 solution (2 ml) was added to he residue. The solid was filtered off with suction and dried under reduced pressure at 60° C. to result in 2-(3-(4-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyric acid (0.25 g; 0.66 mmol). MS: 383.10 (M+H); Rt: 1.57 min (method: gradient 0 min 90% H2O (0.05% TFA) 1.9 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 10% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)
Workup
- customThe solvent was removed under reduced pressure, and saturated NaH2PO4 solution (2 ml)
- additionwas added to he residue
- filtrationThe solid was filtered off with suction
- customdried under reduced pressure at 60° C.
Sources & evidence
- ORD record
- ord-ac34fca295c3412cabff067fa2c05935
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652143B2
Reaction notes
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