Methanol → 3-[4-(Azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid
Reaction equation
[N:1]1([C:5]([C:7]2[CH:31]=[CH:30][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]4[CH2:27][CH2:26][N:25]([CH3:28])[C:24]4=[O:29])[CH:21]=3)[C:15]([O:17]C)=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.CO.O>C1COCC1.[OH-].[Li+]>[N:1]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]4[CH2:27][CH2:26][N:25]([CH3:28])[C:24]4=[O:29])[CH:21]=3)[C:15]([OH:17])=[O:16])=[CH:30][CH:31]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl 3-[4-(azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 16) (309 mg, 0.73 mmol) was dissolved in THF (6 mL) and methanol (2 mL) and IN lithium hydroxide (0.88 mL) was added followed by water (8 mL). The resultant solution was stirred for 1 hr at room temperature. The majority of the organic solvent was removed by distillation under reduced pressure. The remaining aqueous solution was filtered and acidified with 2N hydrochloric acid and extracted with ethyl acetate (2×40 mL), the combined organics were washed with water (10 mL) and brine (20 mL) and dried (MgSO4) to afford the product (298 mg, 100%). m/z 411 (M+H)+
Workup
- customThe majority of the organic solvent was removed by distillation under reduced pressure
- filtrationThe remaining aqueous solution was filtered
- extractionextracted with ethyl acetate (2×40 mL)
- washthe combined organics were washed with water (10 mL) and brine (20 mL)
- dry with materialdried (MgSO4)
Sources & evidence
- ORD record
- ord-a813d9ae9d4c47f388076d702fc4dfa0
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902200B2
Reaction notes
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