Hydrochloric Acid → HCID 58370108, compound

HRID 2062080Notes

Reaction equation

HRID 2062080 reaction equation
C[O:2][C:3](=[O:31])[C:4]([NH:7][C:8]([C:10]1[S:14][C:13]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:12]=2[C:11]=1[O:20][CH2:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1)=[O:9])([CH3:6])[CH3:5].Cl>CO.[OH-].[Na+]>[S:23]1[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=[C:22]1[CH2:21][O:20][C:11]1[C:12]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:13]=2[S:14][C:10]=1[C:8]([NH:7][C:4]([CH3:6])([CH3:5])[C:3]([OH:31])=[O:2])=[O:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66701215HCID 66701215, compound

Product 1

HCID 58370108HCID 58370108, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

138 mg 2-{[3-(Benzothiazol-2-ylmethoxy)-5-fluoro-benzo[b]thiophene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester in 2 ml methanol and 1 ml 1 M aqueous sodium hydroxide solution was refluxed for 0.5 h. The reaction was acidified with 2 M hydrochloric acid, and the precipitated product was collected by filtration, dissolved in ethyl acetate, dried over sodium sulphate adding also active charcoal, filtrated, concentrated in vacuo, and the resulting crude product was crystallized from diethylether to yield 0.08 g 2-{[3-(Benzothiazol-2-ylmethoxy)-5-fluoro-benzo[b]thiophene-2-carbonyl]-amino}-2-methyl-propionic acid.

Workup

  1. filtrationthe precipitated product was collected by filtration
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialdried over sodium sulphate adding also active charcoal
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customthe resulting crude product was crystallized from diethylether

Sources & evidence

ORD record
ord-02832b8aa85e4b00909b8191ad53dffb
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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