Acetic Acid → (S)-3-tert-butoxycarbonylamino-2-(4-isobutyrylpiperazin-1-yl)propanoic acid
Reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([NH:10][CH2:11][C@H:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[CH2:19][CH2:18]1)[C:13]([O:15]C)=[O:14])=[O:9])([CH3:6])([CH3:5])[CH3:4].C(O)(=O)C>O1CCCC1.O>[C:3]([O:7][C:8]([NH:10][CH2:11][C@H:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:27])[CH:24]([CH3:25])[CH3:26])[CH2:19][CH2:18]1)[C:13]([OH:15])=[O:14])=[O:9])([CH3:6])([CH3:5])[CH3:4]Participants
6
Procedure
10 ml (10 mmol) of an aqueous solution of lithium hydroxide having a concentration of 1N are added to a solution of 2.0 g (5.6 mmol) of methyl (S)-3-tert-butoxycarbonylamino-2-(4-isobutyrylpiperazin-1-yl)propanoate in 40 ml of tetrahydrofuran and 8 ml of water, and then the reaction medium is stirred at ambient temperature for 20 h. After the addition of an aqueous solution of acetic acid having a concentration of 1N, the product is extracted with n-butanol. The organic phase is dried over magnesium sulfate, filtered and concentrated under vacuum, 1.5 g (78%) of (S)-3-tert-butoxycarbonylamino-2-(4-isobutyrylpiperazin-1-yl)propanoic acid are obtained in the form of a white solid.
Workup
- extractionthe product is extracted with n-butanol
- dry with materialThe organic phase is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum, 1.5 g (78%) of (S)-3-tert-butoxycarbonylamino-2-(4-isobutyrylpiperazin-1-yl)propanoic acid
- customare obtained in the form of a white solid
Sources & evidence
- ORD record
- ord-2c4930280aea42aeaaabb34240ed3ff3
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420632B2
Reaction notes
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