Sodium Hydroxide → N-[3-carboxy-2-(2-methylpropyl)butanoyl]-O-methyl-L-tyrosine N-methylamide
Reaction equation
[CH3:1][NH:2][C:3](=[O:29])[C@H:4]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[NH:5][C:6](=[O:19])[CH:7]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH:8]([C:10]([O:12]CC)=[O:11])[CH3:9].[OH-].[Na+]>CO>[CH3:1][NH:2][C:3](=[O:29])[C@H:4]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[NH:5][C:6](=[O:19])[CH:7]([CH2:15][CH:16]([CH3:17])[CH3:18])[CH:8]([C:10]([OH:12])=[O:11])[CH3:9]Participants
4
Procedure
N-[3-(Ethoxycarbonyl)-2-(2-methylpropyl)butanoyl]-O-methyl-L-tyrosine N-methylamide (2.0 g., 0.0051 mol.) was hydrolysed upon the addition of methanol (30 mls.) containing 0.1M sodium hydroxide solution (6 mls., 0.006 mol.). The solvent was removed by evaporation in vacuo and the resulting gum washed with diethyl ether (2×25 mls.) The gum was acidified with 0.1M hydrochloric acid solution and the mixture was extracted with dichloromethane (2×50 mls.). The combined extracts were dried over anhydrous sodium sulfate and the solvent was removed by evaporation in vacuo to yield N-[3-carboxy-2-(2-methylpropyl)butanoyl]-O-methyl-L-tyrosine N-methylamide as a mixture of isomers as an off-white solid (1.9 g., 0.0052 mol.).
Workup
- customThe solvent was removed by evaporation in vacuo
- washthe resulting gum washed with diethyl ether (2×25 mls.) The gum
- extractionthe mixture was extracted with dichloromethane (2×50 mls.)
- dry with materialThe combined extracts were dried over anhydrous sodium sulfate
- customthe solvent was removed by evaporation in vacuo
Sources & evidence
- ORD record
- ord-8339507db2ed4d45b1c75e6c1046ceee
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04743587
Reaction notes
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