Diisopropylethylamine → {[2-(Tert-butoxycarbonyl-methyl-amino)acetyl]-methyl-amino}-acetic acid ethyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([OH:13])=O)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:47]([O:49][C:50](=[O:54])[CH2:51][NH:52][CH3:53])[CH3:48]>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:47]([O:49][C:50](=[O:54])[CH2:51][N:52]([C:11](=[O:13])[CH2:10][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:9])[CH3:53])[CH3:48]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To (tert-butoxycarbonyl-methyl-amino)-acetic acid (2.73 g, 14.4 mmol) in 70 mL of THF was added sequentially diisopropyl ethylamine (7.5 mL, 14.4 mmol) and HBTU (5.47 g, 14.4 mmol), and the reaction mixture was stirred at room temperature for one hour. To this reaction mixture was added methylamino-acetic acid ethyl ester (2.22 g, 14.4 mmol) in one portion, and the reaction mixture was heated at 65° C. for 12 h. The reaction mixture was cooled, diluted with a solution of saturated NaHCO3, and extracted with EtOAc. The organic layer was separated and dried over Na2SO4, and the solvent was removed under reduced pressure to give {[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid ethyl ester.
Workup
- temperaturethe reaction mixture was heated at 65° C. for 12 h
- temperatureThe reaction mixture was cooled
- extractionextracted with EtOAc
- customThe organic layer was separated
- dry with materialdried over Na2SO4
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-a1aac02a02944622839d7094b9b88dce
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283354B2
Reaction notes
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