Triethylamine → HCID 22852536, compound

HRID 1654225Notes

Reaction equation

HRID 1654225 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:19])([C@H:16]([SH:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(N(CC)CC)C.[C:27](Cl)(=[O:31])[CH:28]([CH3:30])[CH3:29]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:19])([C@H:16]([S:18][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 1922642-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Product 1

HCID 22852536HCID 22852536, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (5 ml) was dissolved (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol (143 mg), followed by addition of triethylamine (0.076 ml) and isobutyryl chloride (58.6 mg) under ice-cooling. The mixture was stirred at room temperature for 15 minutes, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane-ethyl acetate=1:2). The desired fraction was concentrated to give (2R,3R)-2-(2,4-difluorophenyl)-3-isobutyrylthio-1-(1H-1,2,4-triazol-1-yl)-2-butanol (compound 62, 140 mg) as a colorless syrup. This product was treated with 4N hydrochloric acid (in ethyl acetate) to give the hydrochloride, which was then crystallized from ether to give compound 62 hydrochloride (156 mg) as a colorless powder. m.p. 129°-138° C.

Workup

  1. temperaturecooling
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel chromatography (eluent:hexane-ethyl acetate=1:2)
  4. concentrationThe desired fraction was concentrated

Sources & evidence

ORD record
ord-599674970532475fbdbb2baa7aa3f4f2
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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