Gamma-Aminobutyric Acid → 4-(((Tert-butoxy)carbonyl)amino)butanoic acid
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[O:8](C(OC(C)(C)C)=O)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O.C(N(CC)CC)C>CO>[C:9]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
NH2—(CH2)3—COOH (5.00 g, 48.5 mmol), (BOC)2O (11.6 g, 53.4 mmol) and triethylamine (5.39 g, 53.4 mmol) were dissolved in 200 mL of methanol, and the mixture was stirred at 60° C. for 12 hours. After the reaction completed, methanol was removed under reduced pressure, and the obtained material was redissolved in 100 mL of ethyl acetate. Then, the resultant solution was subjected to separation using 0.2 mol/l HCl (twice) and water (twice), and dehydrating was carried out with anhydrous sodium sulfate. After that, recrystallization with hexane at 4° C. and collection using a glass filter (G6) were performed, thereby obtaining Boc-NH—(CH2)3—COOH (6.98 g, 34.4 mmol, yield: 71%).
Workup
- custommethanol was removed under reduced pressure
- dissolutionthe obtained material was redissolved in 100 mL of ethyl acetate
- customThen, the resultant solution was subjected to separation
- customAfter that, recrystallization with hexane at 4° C.
- customcollection
- filtrationfilter (G6)
Sources & evidence
- ORD record
- ord-4c8b6e41bffa4c89a70b80156d0204ee
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338643B2
Reaction notes
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