Triethylamine → HCID 131720771, compound

HRID 1957256Notes

Reaction equation

HRID 1957256 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19](Cl)(=[O:21])=[O:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.[CH2:24]([O:26][C:27](=[O:31])[CH:28]([CH3:30])[NH2:29])[CH3:25].C(N(CC)CC)C>O1CCCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=2)=[CH:13][C:14]=1[S:19]([NH:29][CH:28]([CH3:30])[C:27]([O:26][CH2:24][CH3:25])=[O:31])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 102560Alanine, ethyl ester, hydrochloride (1:1)HCID 19068779HCID 19068779, compound

Product 1

HCID 131720771HCID 131720771, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.0 g of 3-chloro-2-(4-chloro-3-chlorosulfonylphenyl)-5-trifluoromethylpyridine, 2.4 g of D,L-alanine ethyl ester hydrochloride and 5.2 g of triethylamine in 50 ml of anhydrous tetrahydrofuran were stirred at 23° C. for 18 hours, after which the mixture was concentrated. The residue was taken up in 100 ml of methylene chloride. The solution was extracted twice with 30 ml of water each time, dried over sodium sulfate and concentrated. Chromatography of the residue on silica gel with cyclohexane/ethyl acetate (4:1) resulted in 2.8 g of a colorless oil. Yield: 58%;

Workup

  1. concentrationafter which the mixture was concentrated
  2. extractionThe solution was extracted twice with 30 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-12cad75864194812950e108fc5fabd32
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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