Dimethylformamide → HCID 86585253, compound

HRID 1018247Notes

Reaction equation

HRID 1018247 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-ded8933402df4137a3fc6a568f9c3384
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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