Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 53893355, compound

HRID 379658Notes

Reaction equation

HRID 379658 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]([OH:26])([C@H:17]([O:19]C1CCCCO1)[CH3:18])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@:10]([OH:26])([C@H:17]([OH:19])[CH3:18])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 9799558HCID 9799558, compound

Product 1

HCID 53893355HCID 53893355, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of (3R)-2-(2,4,5-trifluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (740 mg) and pyridinium p-toluene sulfonate (PPTS, 200 mg) in ethanol (15 ml) was heated at 55° C. for 7 h. The reaction mixture was partitioned between ethyl acetate and water. The water layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, and concentrated to dryness in vacuo. Purification of the residue by silica gel chromatography, using dichloromethane:methanol (20:1) as an eluent, gave (2R,3R)-2-(2,4,5-trifluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (361 mg, 63%) as white amorphous.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe water layer was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness in vacuo
  5. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-6b61015933b345e5991b2a6dd201292a
Source dataset
uspto-grants-2001_10
Patent number
US06300353B1

Reaction notes

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