Lithium Hydroxide → 17-Ethoxymethoxy-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]-octadec-7-ene-4-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[CH:13]1[CH:9]([CH2:10][CH:11]([O:26][CH2:27][O:28][CH2:29][CH3:30])[CH2:12]1)[C:8](=[O:31])[NH:7]2)=[O:5])C.[Li+].[OH-]>C1COCC1.CO>[CH2:29]([O:28][CH2:27][O:26][CH:11]1[CH2:10][CH:9]2[CH:13]([C:14](=[O:25])[N:15]([CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][CH:22]3[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]2=[O:31])[CH2:23]3)[CH2:12]1)[CH3:30]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of the ester (115) (1.48 g, 3.39 mmol) in 1:1:1 THF-methanol-aq. 1M LiOH (102 ml) was stirred at 60° C., then at room temperature overnight. The reaction mixture was then concentrated into approximately ⅓ of the volume, diluted with water (30 ml) and acidified to approx. pH 4 using aq. 10% citric acid (60 ml), then washed with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (1×100 ml), then dried (Na2SO4), filtered and concentrated. Column chromatography of the residue using 9:1 ethyl acetate-methanol as eluent gave the title compound as a slight yellow (The coloring from the previous step was removed during work up and chromatography). Yield: 1.35 g, 97%. LR-MS: Calcd for C21H31N2O6: 407. Found: 407 [M−H].
Workup
- customat room temperature
- customovernight
- concentrationThe reaction mixture was then concentrated into approximately ⅓ of the volume
- additiondiluted with water (30 ml)
- washwashed with ethyl acetate (3×50 ml)
- washThe combined organic layers were washed with brine (1×100 ml)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c44d4d004564423183b7bbfb059a1a83
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07666834B2
Reaction notes
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