N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → 3-[2-(Tert-butoxycarbonylamino)acetyl]amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine
Reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[N:9][N:10]2[CH2:15][CH2:14][CH2:13][NH:12][C:11]=12.C(N(C(C)C)C(C)C)C.[C:25]([O:29][C:30]([NH:32][CH2:33][C:34](ON1C(=O)CCC1=O)=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([O:29][C:30]([NH:32][CH2:33][C:34]([NH:6][C:7]1[CH:8]=[N:9][N:10]2[CH2:15][CH2:14][CH2:13][NH:12][C:11]=12)=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine sulfuric acid salt (2.96 g) and N-ethyldiisopropylamine (2.59 g) in methylene chloride (70 ml) was added N-[2-(tert-butoxycarbonylamino)acetoxy]succinimide (2.72 g). The mixture was stirred at room temperature for 14 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 6% methanol/chloroform to give 3-[2-(tert-butoxycarbonylamino)acetyl]amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (2.4 g) as a solid.
Workup
- washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel eluting with 6% methanol/chloroform
Sources & evidence
- ORD record
- ord-6966be87f7f7422da598bd7bd1e322b9
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129232B2
Reaction notes
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