Hydrochloric Acid → (+/-)-3-Carboxymethyl-4-(3,5-dichloro-4-pyridylamino-carbonyl)-7-methoxy-2,3-dihydrobenzofuran

HRID 2084750

Reaction equation

HRID 2084750 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:28])[C:7]=1[NH:8][C:9]([C:11]1[C:16]2[CH:17]([CH2:20][C:21]([O:23]CC)=[O:22])[CH2:18][O:19][C:15]=2[C:14]([O:26][CH3:27])=[CH:13][CH:12]=1)=[O:10].[OH-].[Na+].Cl>>[C:21]([CH2:20][CH:17]1[C:16]2[C:11]([C:9]([NH:8][C:7]3[C:6]([Cl:28])=[CH:5][N:4]=[CH:3][C:2]=3[Cl:1])=[O:10])=[CH:12][CH:13]=[C:14]([O:26][CH3:27])[C:15]=2[O:19][CH2:18]1)([OH:23])=[O:22]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22734397(+/-)-4-[(3,5-Dichloro-4-pyridyl)aminocarbonyl]-3-ethoxycarbonylmethyl-7-methoxy-2,3-dihydrobenzofuran

Product 1

HCID 22734342(+/-)-3-Carboxymethyl-4-(3,5-dichloro-4-pyridylamino-carbonyl)-7-methoxy-2,3-dihydrobenzofuranYield 98.3%

Procedure

Compound 5 (0.329 g) obtained in Example 5 was mixed with a 2N aqueous solution of sodium hydroxide (6.6 ml), followed by stirring at room temperature for one hour. Under ice-cooling, the reaction mixture was adjusted to pH 2 by adding hydrochloric acid, and then the precipitated solid was collected by filtration. The obtained crude product was recrystallized from ethanol to give Compound 9 (0.302 g, 98%) as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. filtrationthe precipitated solid was collected by filtration
  3. customThe obtained crude product
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-6e19521d07154ea29fcb5fbffa7d57cc
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Linked notes

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