Methanol → HCID 4187566, compound

HRID 401608Notes

Reaction equation

HRID 401608 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[C:8]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[CH3:21]O>C(=O)(O)[O-].[Na+]>[CH3:21][O:4][C:3](=[O:5])[CH:2]([NH2:1])[CH2:6][C:7]1[C:8]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 4270942-amino-3-(5-chloro-1-benzothiophen-3-yl)propanoic acid

Product 1

HCID 4187566HCID 4187566, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 2-Amino-3-(5-chloro-benzo[b]thiophen-3-yl)-propionic acid (255.7 mg, 1.0 mmol) in methanol was added thionyl chloride (0.08 mL) at 0° C. The resulting mixture was heated at reflux for 7 h, allowed to cool to room temperature, diluted with saturated sodium bicarbonate and extracted with ethyl acetate (2×30 mL). The organic extracts were combined, washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give a yellow oil (2-amino-3-(5-chloro-benzo[b]thiophen-3-yl)-propionic acid methyl ester).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 7 h
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. washwashed with brine (25 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b9d070ad1b7541daace26b38e6ee74c1
Source dataset
uspto-grants-2014_06
Patent number
US08741942B2

Reaction notes

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