Triethylamine → HCID 10578947, compound

HRID 1489428Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:34])([CH2:32][OH:33])[C@H:10]([N:12]1[C:16](=[O:17])[N:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])=[CH:20][CH:19]=2)[CH:14]=[N:13]1)[CH3:11].[CH3:35][S:36](Cl)(=[O:38])=[O:37].C(N(CC)CC)C>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:34])([CH2:32][O:33][S:36]([CH3:35])(=[O:38])=[O:37])[C@H:10]([N:12]1[C:16](=[O:17])[N:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])=[CH:22][CH:23]=2)[CH:14]=[N:13]1)[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

2-[(1R,2S)-2-(2,4-Difluorophenyl)-2,3-dihydroxy-1-methylpropyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (8.26 g) was dissolved in 100 ml of ethyl acetate, to which 2.89 g of methanesulfonyl chloride and 2.54 g of triethylamine were added dropwise with ice cooling. After stirring at 0° C. for 30 minutes, the solution was washed with water (20 ml×2) and 20 ml of an aqueous solution of sodium chloride successively. The organic layer was dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give 10 g of 2-[(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-3-methanesulfonyloxy-1-methylpropyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone as a colorless oil.

Workup

additionwere added dropwise with ice cooling
washthe solution was washed with water (20 ml×2) and 20 ml of an aqueous solution of sodium chloride successively
dry with materialThe organic layer was dried over magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-cf08fd39866a4aafac18270d1c8486bd
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05677464

Reaction notes

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