Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | N2-Acetyl-D-asparagine | HCID 117735 | — |
| Reactant | 6-(4-Aminophenyl)-1,2-dihydro-2-oxonicotinic acid | HCID 12918956 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Solvent | Isobutyl chloroformate | HCID 62365 | — |
| Product | HCID 13002092 | HCID 13002092 | — |
Reaction Steps
The silylated derivative of 6-(4-aminophenyl)-1,2-dihydro-2-oxonicotinic acid in 70 ml dichloromethane is added to a mixed anhydride prepared from N-Acetyl-D-asparagine 3.5 g (20 m mol), N-methylmorpholine 2.2 ml (20 m mol) in 50 ml N,N-dimethylacetamide and isobutyl chloroformate 2.9 ml (22 m mol) by stirring at 5° C. for 1 hr and 3 hrs at room temperature. Next 20 ml of isopropanol is added and the reaction mixture evaporated. Water is added to the residue and the mixture filtered. After recrystallization from N,N-dimethylacetamide MeOH, 1.8 g of 6-[4-(N-Acetyl-D-asparaginylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid is obtained, m.p. 265°-266° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04311698 |
|---|
| Source dataset | uspto-grants-1982_01 |
|---|
| ORD ID | ord-9348383eb3ee4c739f7a0457a3e5abe1 |
|---|
| Source note | uspto-grants-1982_01 |
|---|
