Hydrochloric Acid → N-(2quinolinylcarbonyl)-L-isoasparagine

HRID 265268

Reaction equation

HRID 265268 reaction equation
[NH2:1][C@H:2]([C:7](=[O:9])[NH2:8])[CH2:3][C:4]([OH:6])=[O:5].O.C(=O)(O)[O-].[C:15](O)(=[O:26])[C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.Cl>COCCOC>[N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1[C:15]([NH:1][C@H:2]([C:7](=[O:9])[NH2:8])[CH2:3][C:4]([OH:6])=[O:5])=[O:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 962WaterHCID 7124Quinaldic AcidHCID 7015702Isoasparagine

Product 1

HCID 59936550N-(2quinolinylcarbonyl)-L-isoasparagineYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 0.50 g (3.78 mmol) of L-isoasparagine in 5.0 mL H2O containing ~45 mg (1.5 eq) of solid bicarbonate. To this was added a suspension of 1.02 g (3.78 mmol) quinaldic acid, N-hydroxysuccinamide ester in ethylene glycol dimethylether, and the suspension was solubilized by the addition of 10 mL of dimethyfformamide. After 3 hours the solution was acidified by the addition of 5% HCl (aqueous) and the product was filtered and washed with water, dried under vacuum to yield 750 mg (70% yield) of N-(2-quinolinylcarbonyl)-L-isoasparagine.

Workup

  1. additionTo this was added
  2. additionthe suspension was solubilized by the addition of 10 mL of dimethyfformamide
  3. filtrationthe product was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ce810b99662841ceb2a3a0a35cbead99
Source dataset
uspto-grants-1997_07
Patent number
US05648364

Linked notes

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