Sodium Hydroxide → HCID 45256346, compound

HRID 2065666Notes

Reaction equation

HRID 2065666 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:18][CH:19]([C:30]([OH:32])=[O:31])[CH2:20][C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=2[CH3:17])=[O:5])C.[OH-].[Na+]>C1COCC1>[C:30]([CH:19]([NH:18][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:15][C:14]2[C:9](=[C:10]([CH3:17])[CH:11]=[C:12]([Cl:16])[CH:13]=2)[N:8]=1)[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67359615HCID 67359615, compound

Product 1

HCID 45256346HCID 45256346, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In close analogy to the procedure described in Example 32, 2,6-dichloro-8-methyl-quinoline-3-carboxylic acid ethyl ester is reacted with DL-tryptophan to provide 2-[1-carboxy-2-(1H-indol-3-yl)-ethylamino]-6-chloro-8-methyl-quinoline-3-carboxylic acid ethyl ester. The ester (107 mg, 0.24 mmol) is dissolved in THF (2 mL), then 0.7M aqueous NaOH (1 mL) is added and the mixture is stirred at rt for 23 h. The mixture is concentrated under reduced pressure treated with water and filtered. The filtrate is acidified by addition of 3N HCl till pH 2-3, and stirred for 40 min. Precipitate is filtered off and washed with cold water to provide after drying the title compound (55 mg, 61%) as pale green powder.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additiontreated with water
  3. filtrationfiltered
  4. additionThe filtrate is acidified by addition of 3N HCl till pH 2-3
  5. stirringstirred for 40 min
  6. filtrationPrecipitate is filtered off
  7. washwashed with cold water
  8. customto provide
  9. dry with materialafter drying the title compound (55 mg, 61%) as pale green powder

Sources & evidence

ORD record
ord-de0a81cbac2d4a7ba2f23ead6281c8eb
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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