Hydrochloric Acid → HCID 58370108, compound

HRID 2075512Notes

Reaction equation

HRID 2075512 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 1M 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 diethyl-ether 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 diethyl-ether

Sources & evidence

ORD record
ord-cb44852abf5e42e48fb99131e13f48da
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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