Hydrochloric Acid → HCID 86645992, compound

HRID 1800433Notes

Reaction equation

HRID 1800433 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([O:16][C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[C:20]([O:22]C)=[O:21])[N:10]=3)=[O:5])[CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+].Cl>CO>[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([O:16][C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[C:20]([OH:22])=[O:21])[N:10]=3)=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86645993HCID 86645993, compound

Product 1

HCID 86645992HCID 86645992, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methoxybenzoate (4.0 g, 9.96 mmol) in methanol (50 mL)-tetrahydrofuran (100 mL) was added 5N aqueous sodium hydroxide solution (80 mL), and the mixture was stirred at room temperature for 3 hr. 6N Hydrochloric acid was added to the reaction solution to adjust the pH to about 4.0, and the reaction solution was extracted with ethyl acetate (200 mL×3). The combined organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated to give the title compound (3.70 g, 96%) as a yellow solid.

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate (200 mL×3)
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. filtrationthe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bcd40db6d3244bec9cae89e188e2a6dc
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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