Dimethylformamide → HCID 86585253, compound

HRID 1280072Notes

Reaction equation

HRID 1280072 reaction equation
[ClH:1].[N:2]([C:5]1[CH:16]=[CH:15][C:8]([CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:7][CH:6]=1)=[N+:3]=[N-:4].[C:17]([O:21][CH3:22])(=[O:20])[C:18]#[CH:19].[CH3:23]N(C=O)C>>[Cl-:1].[CH3:23][O:13][C:12]([C@@H:10]([NH3+:11])[CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N:2]2[CH:19]=[C:18]([C:17]([O:21][CH3:22])=[O:20])[N:4]=[N:3]2)=[CH:16][CH:15]=1)=[O:14]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 13536Methyl propiolateHCID 865852544-Azido-L-phenylalanine (hydrochloride)

Product 1

HCID 86585253HCID 86585253, compoundYield 53%

Conditions

Temperature
45 °C

Procedure

4-Azido-L-phenylalanine hydrochloride (0.242 g, 1 mmol) was dissolved in dry DMF (1 mL) and methyl propiolate (0.420 g, 5 mmol) was added. The suspension was stirred 24 h at 45 ° C. After cooling to room temperature, the solid was filtered, washed with EtOAc and dried (175 mg). The material was suspended in MeOH (15 mL) and thionyl chloride (0.5 mL) was added drop-wise. The mixture was refluxed for 3 h, cooled and concentrated under reduced pressure. The residue was triturated with ether to give the title compound as a white solid (175 mg, 53% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was filtered
  3. washwashed with EtOAc
  4. customdried (175 mg)
  5. additionthionyl chloride (0.5 mL) was added drop-wise
  6. temperatureThe mixture was refluxed for 3 h
  7. temperaturecooled
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-af95c9178bf74d06b8331e7e7c97c774
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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