Triethylamine → HCID 10450288, compound

HRID 2397002Notes

Reaction equation

HRID 2397002 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]([OH:18])([C@H:15]([OH:17])[CH3:16])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(OCC)(=O)C>[CH3:26][S:27]([O:17][C@H:15]([CH3:16])[C@:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([OH:18])[CH2:9][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10400800HCID 10400800, compound

Product 1

HCID 10450288HCID 10450288, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,3R)-2-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (12.4 g) and triethylamine (7.6 ml) in ethyl acetate (200 ml) was added dropwise methanesulfonyl chloride (6.25 g) under ice-cooling. After stirring for 45 minutes at room temperature, the reaction mixture was washed with water and saturated saline, dried over magnesium sulfate and distilled under reduced pressure to give (2R,3R)-2-(4-chlorophenyl)-2-hydroxy-1-(1H-1,2,4-triazol-1-yl)-3-butyl methanesulfonate.

Workup

  1. temperaturecooling
  2. washthe reaction mixture was washed with water and saturated saline
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-7ec2880284e34e8bb0b9a7c4d5492c69
Source dataset
uspto-grants-1996_02
Patent number
US05495024

Reaction notes

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