Pyridine → HCID 86752927, compound

HRID 1957270Notes

Reaction equation

HRID 1957270 reaction equation
Cl[C:2]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19](Cl)=[O:20])[CH:13]=2)[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][NH:3]1.[ClH:22].[CH2:23]([O:25][C:26](=[O:32])[C@H:27]([CH:29]([CH3:31])[CH3:30])[NH2:28])[CH3:24].N1C=CC=CC=1>C(Cl)Cl>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:2]2[C:7]([Cl:22])=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=2)=[CH:13][C:14]=1[C:19]([NH:28][C@@H:27]([CH:29]([CH3:31])[CH3:30])[C:26]([O:25][CH2:23][CH3:24])=[O:32])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 87181Ethyl L-valinate hydrochlorideHCID 19068728HCID 19068728, compound

Product 1

HCID 86752927HCID 86752927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3.55 g of 2-chloro-2-(4-chloro-3-chloroformylphenyl)-5-trifluoromethylpyridine in 10 ml of methylene chloride was added dropwise to a mixture of 3.63 g of L-valine ethyl ester hydrochloride, 7.9 g of pyridine and 30 ml of methylene chloride at 23° C. After stirring for 60 hours, 160 ml of methylene chloride were added. The mixture was washed three times with 150 ml of water each time, dried over sodium sulfate and then concentrated. The crude product was purified by chromatography on silica gel with cyclohexane/ethyl acetate (10:1). Yield: 2.2 g (48%) of colorless crystals; melting point: 90°-92° C.

Workup

  1. washThe mixture was washed three times with 150 ml of water each time
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by chromatography on silica gel with cyclohexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-dff59fc86e3e4b6db0d6a7718de8a52e
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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