Lithium hydroxide, monohydrate → 5-[2-(tert-Butoxycarbonyl-ethyl-amino)-propyl]-benzo[1,3]dioxole-2-carboxylic acid
Reaction equation
C([O:3][C:4]([CH:6]1[O:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][CH:16]([N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH3:20])[CH3:17])=[CH:14][C:8]=2[O:7]1)=[O:5])C.O.[OH-].[Li+]>CO.O>[C:24]([O:23][C:21]([N:18]([CH2:19][CH3:20])[CH:16]([CH3:17])[CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[O:10][CH:6]([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:14]=1)=[O:22])([CH3:26])([CH3:27])[CH3:25]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 50 mg (0.13 mmol) of 2D in 2 mL of 50% methanol in water was added 50 mg (1.19 mmol) of lithium hydroxide monohydrate. The mixture was allowed to stir at room temperature 18 hours and was concentrated under reduced pressure. To the residue was added 10 mL of water, and the pH was adjusted to 6 using phosphoric acid. The resulting aqueous solution was extracted with 2×25 mL of chloroform. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to give 41 mg (0.12 mmol, 82%) of 2M as a thick colorless gum.
Workup
- concentrationwas concentrated under reduced pressure
- additionTo the residue was added 10 mL of water
- extractionThe resulting aqueous solution was extracted with 2×25 mL of chloroform
- dry with materialThe combined organic layers were dried (Na2SO4)
- concentrationconcentrated under reduced pressure
- customto give 41 mg (0.12 mmol, 82%) of 2M as a thick colorless gum
Sources & evidence
- ORD record
- ord-3af9ebb41af14e2cb3b2b7e9bd8e6cdf
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07060847B2
Reaction notes
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