1,4-Dioxane hydrochloride → HCID 57868408, compound

HRID 1091317Notes

Reaction equation

HRID 1091317 reaction equation
C([O:5][C:6](=[O:26])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[S:20][CH:21]=2)=[O:16])=[CH:10][CH:9]=1)(C)(C)C.Cl.[O:28]1CCOC[CH2:29]1>C(Cl)(Cl)Cl>[S:20]1[CH:21]=[C:17]([C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][C:6]([OH:5])=[O:26])=[CH:9][C:10]=2[O:28][CH3:29])=[O:16])[C:18]2[CH:25]=[CH:24][CH:23]=[CH:22][C:19]1=2

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66592392HCID 66592392, compound

Product 1

HCID 57868408HCID 57868408, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-[(Benzo[b]thiophen-3-ylcarbonyl)amino]phenylacetic acid tert-butyl ester (2.12 g, 5.33 mmol) and a 4N—HCl-dioxane solution (20 mL) were mixed, and the mixture was stirred for hours at room temperature, and for 8 hours at 70° C. After cooling the mixture naturally, the mixture was diluted with chloroform (200 mL), washed with water (100 mL) and saturate brine (100 mL), and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified with a column (40S) of Biotage AB (5% methanol-chloroform), to obtain the title compound (3.47 g, 94%) as a crystalline powder.

Workup

  1. temperatureAfter cooling the mixture naturally
  2. washwashed with water (100 mL)
  3. concentrationsaturate brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified with a column (40S) of Biotage AB (5% methanol-chloroform)

Sources & evidence

ORD record
ord-7a076b3a8a71405faa1090568df0f18f
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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