Acetic Acid → 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(1,6-naphthyridin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acid
Reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[N:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([S:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([O:37]C)=[O:36])=[CH:4][CH:3]=1.CO.[Li+].[OH-].CC(O)=O>C1COCC1.O>[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[N:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([S:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([OH:37])=[O:36])=[CH:4][CH:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The compound from Step 2 (280 mg) was hydrolyzed by dissolving it in THF (3 mL), MeOH (1.5 mL), and 2N LiOH (0.27 mL) and heating at 70° C. for 6 hours. The solution was cooled to room temperature, diluted with H2O (50 mL), acidified with glacial AcOH to pH 5 and then diluted with 25% aqueous NH4OAc (50 mL). The mixture was extracted with ethyl acetate (3×50 mL), washed with brine (50 mL), and dried (MgSO4). The solution was evaporated to dryness and coevaporated with toluene (50 mL) to provide the title acid as a white solid; m.p. 204° C. (dec.).
Workup
- extractionThe mixture was extracted with ethyl acetate (3×50 mL)
- washwashed with brine (50 mL)
- dry with materialdried (MgSO4)
- customThe solution was evaporated to dryness
Sources & evidence
- ORD record
- ord-20c567ebdc31498892b4668ed25b6a64
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05273980
Reaction notes
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