Pyridine → HCID 58665196, compound

HRID 1622904Notes

Reaction equation

HRID 1622904 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]([NH:5][C@H:6]([CH3:10])[C:7](O)=[O:8])=[O:4].N1C=CC=CC=1.C(Cl)(=O)C([Cl:22])=O>ClCCl>[F:1][C:2]([F:12])([F:11])[C:3]([NH:5][C@H:6]([CH3:10])[C:7]([Cl:22])=[O:8])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 13774519HCID 13774519, compound

Product 1

HCID 58665196HCID 58665196, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound obtained in step 1) (17.2 g, 0.0845 mol) was dissolved in 300 ml of dichloromethane, and 1 ml of pyridine was added. The reaction mixture was cooled in ice-water bath to 0˜3, and oxalyl chloride (25.8 g, 0.203 mol) was added dropwise. After the completion of the addition, the temperature was slowly raised to room temperature, and a reaction was allowed to proceed for 3 hours. Evaporation was carried out under reduced pressure to remove the solvent, and 50 ml×2 benzene was added to remove residual solvent by azeotropism. The obtained (R)—N-trifluoroacetyl-2-amino propionyl chloride can be directly used for the subsequent reaction.

Workup

  1. additionwas added dropwise
  2. additionAfter the completion of the addition
  3. customEvaporation
  4. customto remove the solvent, and 50 ml×2 benzene
  5. additionwas added
  6. customto remove residual solvent by azeotropism
  7. customThe obtained (R)—N-trifluoroacetyl-2-amino propionyl chloride can be directly used for the subsequent reaction

Sources & evidence

ORD record
ord-63bf8ff9e76d4d768879f8297dff513a
Source dataset
uspto-grants-2014_07
Patent number
US08778948B2

Reaction notes

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