Isopropanol → HCID 13002092, compound

HRID 1106183Notes

Reaction equation

HRID 1106183 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[C:18]([NH:21][C@@H:22]([C:27](O)=[O:28])[CH2:23][C:24](=[O:26])[NH2:25])(=[O:20])[CH3:19].CN1CCOCC1.C(O)(C)C>ClCCl.CN(C)C(=O)C.ClC(OCC(C)C)=O>[C:18]([NH:21][C@@H:22]([C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1)=[O:28])[CH2:23][C:24](=[O:26])[NH2:25])(=[O:20])[CH3:19]

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 79724-MethylmorpholineHCID 117735N2-Acetyl-D-asparagineHCID 129189566-(4-Aminophenyl)-1,2-dihydro-2-oxonicotinic acid

Product 1

HCID 13002092HCID 13002092, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolventHCID 62365Isobutyl chloroformateSolvent

Conditions

Temperature
5 °C

Procedure

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.

Workup

  1. customthe reaction mixture evaporated
  2. additionWater is added to the residue
  3. filtrationthe mixture filtered
  4. customAfter recrystallization from N,N-dimethylacetamide MeOH

Sources & evidence

ORD record
ord-9348383eb3ee4c739f7a0457a3e5abe1
Source dataset
uspto-grants-1982_01
Patent number
US04311698

Reaction notes

Loading…