Lithium Hydroxide → HCID 71294354, compound
Reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[C:8]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:9][CH:10]=1)=[O:4].O1CCCC1.[OH-].[Li+].[NH4+].[Cl-]>O>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([C:7]2[C:8]([O:11][CH2:12][C:13]([F:15])([F:16])[F:14])=[N:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
In a 25 mL round-bottomed flask, the above prepared 2-(2,2,2-trifluoro-ethoxy)-3′,4′,5′,6′-tetrahydro-2′H-[3,4]bipyridinyl-5,1′-dicarboxylic acid 1′-tert-butyl ester 5-methyl ester (1.266 g, 2.42 mmol, Eq: 1.00) was combined with tetrahydrofuran (7 mL) and water (3.5 mL) to give a colorless solution. Lithium hydroxide (145 mg, 6.05 mmol, Eq: 2.5) was added and the reaction mixture was stirred at 40° C. for 3 h when TLC indicated the absence of starting material. Work up: 10 mL H2O and 10 mL sat NH4Cl were added and the reaction mixture was extracted with AcOEt (2×50 ml). The organic layers were washed with H2O/NaCl solution, combined, dried over Na2SO4 and concentrated in vacuo. Crystallization from EtOAc and heptane afforded 800 mg of the title compound as white solid; MS (EI) 403.6 (M−H)−.
Workup
- customto give a colorless solution
- additionwere added
- extractionthe reaction mixture was extracted with AcOEt (2×50 ml)
- washThe organic layers were washed with H2O/NaCl solution
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customCrystallization from EtOAc and heptane
Sources & evidence
- ORD record
- ord-0bc66ddbabed423cb847c9f2847a6b11
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08648099B2
Reaction notes
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