Methanol → HCID 71258976, compound

HRID 526355Notes

Reaction equation

HRID 526355 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:20]O>>[CH3:20][O:5][C:4](=[O:6])[CH2:3][CH:2]([NH2:1])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 71258954HCID 71258954, compound

Product 1

HCID 71258976HCID 71258976, compoundYield 47%

Conditions

Temperature
0 °C

Procedure

436 mg (2.09 mmol) 3-amino-3-(4-cyano-3-fluorophenyl)propionic acid were suspended in 8.5 ml methanol and the mixture cooled to 0° C. 0.23 ml (3.14 mmol) thionyl chloride were slowly added. The mixture was stirred at room temperature for 20 hours and concentrated. The residue was treated with saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic part was dried with sodium sulfate and concentrated. Chromatography over silica gel (dichloromethane/ethanol 100/0-97/3-94/6) gave 245 mg (47%) 3-amino-3-(4-cyano-3-fluoro-phenyl)-propionic acid methyl ester.

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with saturated sodium hydrogen carbonate solution
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic part was dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-29fefe0ad9e24b8aa941b214035b7046
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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