Lithium Hydroxide → (S)-6-(tert-Butoxycarbonyl)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-3-carboxylic acid
Reaction equation
[O:1]=[C:2]1[N:7]2[C@H:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:6]2=[N:5][CH:4]=[C:3]1[C:18]([O:20]C)=[O:19].[Li+].[OH-]>CO>[C:14]([O:13][C:11]([C@H:8]1[N:7]2[C:2](=[O:1])[C:3]([C:18]([OH:20])=[O:19])=[CH:4][N:5]=[C:6]2[CH2:10][CH2:9]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1f (14.15 g, 48.1 mmol) in 250 mL MeOH at 0° C. was slowly added aqueous LiOH (1M, 48 mL, 48 mmol) over 15 min. The reaction was allowed to warm to rt overnight with stirring. The organic solvent was removed in vacuo. The residual aqueous solution was partitioned with Et2O, then the organic phase was extracted with H2O (2×). The combined aqueous extract was acidified to pH 2 with 1N HCl. The aqueous phase was extracted with CHCl3 (3×). The combined organic extract was dried (MgSO4) and concentrated to afford 11.4 g (85%) of the acid, 1g, as a tan crystalline solid.
Workup
- customat 0° C.
- customover 15 min
- customThe organic solvent was removed in vacuo
- customThe residual aqueous solution was partitioned with Et2O
- extractionthe organic phase was extracted with H2O (2×)
- extractionThe combined aqueous extract
- extractionThe aqueous phase was extracted with CHCl3 (3×)
- extractionThe combined organic extract
- dry with materialwas dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4f5a5cd5393c47b4ae9213b8c1fcb765
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06653295B2
Reaction notes
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