Sodium Hydroxide → HCID 19360724, compound
Reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([CH2:8][CH:9]2[C:20](=[O:21])[NH:19][CH2:18][CH2:17][NH:16][C:15](=[O:22])[CH2:14][N:13](C(=O)C(F)(F)F)[C:12](=[O:29])[CH2:11][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+]>>[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([CH2:8][CH:9]2[C:20](=[O:21])[NH:19][CH2:18][CH2:17][NH:16][C:15](=[O:22])[CH2:14][NH:13][C:12](=[O:29])[CH2:11][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
Procedure
The aforementioned free amino acylation affords 3-(4-nitrophenyl)-2-hydroxy-N-(trifluoroacetylglycylglycyl-2-aminoethyl)propionamide. The hydroxyl group of 3-(4-nitrophenyl)-2-hydroxy-N-(trifluoroacetylglycylglycyl-2-aminoethyl)propionamide is tosylated with TsCl in pyridine to give 3-(4-nitrophenyl)-2-(p-toluenesulfonyl)-oxy-N-(trifluoroacetylglycylglycyl-2-aminoethyl)-propionamide. The trifluoroacetylamide group of 3-(5-nitrophenyl)-2-(p-toluenesulfonyl)-oxy-N-(trifluoroacetylglycylglycyl-2-aminoethyl)-propionamide is deprotonated with sodium hydride and cyclized to give 2-(4-nitrobenzyl)-3,8,11-trioxo-N-trifluoroacetyl-1,4,7,10-tetraazadodecane. The trifluoroacetyl group of 2-(4-nitrobenzyl)-3,8,11-trioxo-N-trifluoroacetyl-1,4,7,10-tetraazacyclododecane is cleaved with sodium hydroxide to afford a triamide product, 2-(4-nitrobenzyl)-3,8,11-trioxo-1,4,7,10-tetraazacyclododecane. The triamide is reduced with borane to give 2-(p-nitrophenyl)-1,4,7,10-tetraazacyclododecane. Conversion of this product to nitro-benzyl-DOTA is accomplished via the procedure discussed in the Renn et al. article referenced above or as discussed in subsections A and C set forth above.
Sources & evidence
- ORD record
- ord-3394ab870f6742dea9a54c6de82fae18
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06022966
Reaction notes
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