Quinaldic Acid → Quinoline-2-carbonyl-(L)-asparagine tert-butyl Ester

HRID 1291786Notes

Reaction equation

HRID 1291786 reaction equation
[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[C:39]([O:43][C:44](=[O:51])[C@H:45]([CH2:47][C:48](=[O:50])[NH2:49])[NH2:46])([CH3:42])([CH3:41])[CH3:40]>C1COCC1>[C:39]([O:43][C:44](=[O:51])[C@H:45]([CH2:47][C:48](=[O:50])[NH2:49])[NH:46][C:1]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[O:13])([CH3:42])([CH3:40])[CH3:41]

Participants

6

Reactant 4

HCID 7124Quinaldic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 6995006L-Asparagine tert-butyl ester

Product 1

HCID 54175058Quinoline-2-carbonyl-(L)-asparagine tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Analogously to Example 100, 5.45 g (31.4 mmol) of quinaldic acid in 161 ml of THF are reacted with 7.08 g (34.3 mmol) of DCC, 4.63 g (34.3 mmol) of HOBT and 5.38 g (28.6 mmol) of (L)-asparagine tert-butyl ester (Bachem, Bubendorf/Switzerland). Filtration, extraction and column chromatography (SiO2, ethyl acetate/hexane 3:1) yields the pure title compound: TLC Rf (C')=0.15; tRet (V)=12.2 min; FAB-MS (M+H)+ =344.

Workup

  1. filtrationFiltration, extraction and column chromatography (SiO2, ethyl acetate/hexane 3:1)

Sources & evidence

ORD record
ord-bdb93e3228bb490cb932257cbcdb6efb
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

Loading…