Water → HCID 14348570, compound
Reaction equation
[OH:1][CH:2]([CH:4]([CH:10]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:11]([CH3:17])[C:12]([O:14]CC)=[O:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:3].[OH-].[Ba+2].[OH-].O>O1CCCC1>[CH3:17][CH:11]([CH:10]([NH:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:2]([OH:1])[CH3:3])[C:12]([OH:14])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture (140 mg) of the isomers (10a) and (10b) of diethyl 2-(1-hydroxyethyl)-3-benzylamino-4-methylpentanedioate (10a:10b=5:2) as obtained in Example 14 (2.15 g) was dissolved in tetrahydrofuran (4 ml), barium hydroxide (250 mg) and water (2 ml) were added thereto, and the resultant mixture was stirred vigorously at room temperature of 45 minutes. Insoluble materials were collected by filtration and washed with ethanol. The washing and the filtrate were combined together and concentrated under reduced pressure. The residue was subjected to thin layer chromatography, whereupon a new spot was revealed in addition to the spots corresponding to the starting material and the original point. The product as the new spot was collected and fractionally purified to give (2RS,3RS,4SR,5SR)-2-methyl-3-benzylamino-4-ethoxycarbonyl-5-hydroxyhexanoic acid (70 mg).
Workup
- filtrationInsoluble materials were collected by filtration
- washwashed with ethanol
- concentrationconcentrated under reduced pressure
- additionwas revealed in addition to the spots corresponding to the starting material
- customThe product as the new spot was collected
- customfractionally purified
Sources & evidence
- ORD record
- ord-d475fa2d81dc498fa2f2bbd644792493
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05134231
Reaction notes
Loading…