Hydrochloric Acid → (2R,3R)-2-(2,3-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol

HRID 1936849Notes

Reaction equation

HRID 1936849 reaction equation
Cl.[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C@:10]([OH:32])([C@H:17]([S:19][C@@H:20]1[CH2:25][O:24][C@@H](C2C=CC=CC=2)[O:22][CH2:21]1)[CH3:18])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1>C1(C)C=CC=CC=1>[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C@:10]([OH:32])([C@H:17]([S:19][CH:20]([CH2:21][OH:22])[CH2:25][OH:24])[CH3:18])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178462386HCID 178462386, compound

Product 1

HCID 69943646(2R,3R)-2-(2,3-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

30 ml (30 mmol) of 1 N hydrochloric acid were added to a solution of 3.35 g of crude (2R,3R)-2-(2,3-difluorophenyl)-3-[(trans-2-phenyl-1,3-dioxan-5-yl)thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol [prepared as described in Step 7(v) above] in 45 ml of toluene. The resulting mixture was heated at 50° C. for 6 hours. At the end of this time, the aqueous layer was separated. The oily layer was then extracted twice with a dilute hydrochloric acid solution. The aqueous layers were then combined and sodium hydrogen carbonate was carefully added in small portions to the solution until the evolution of carbon dioxide gas had ceased. The reaction mixture was then extracted with ethyl acetate and the extract was concentrated under reduced pressure to afford the title compound as a solid. The solid was washed with a 2:1 mixture of ethyl acetate and hexane and 1.54 g [overall yield from Step 7(v) 61%] of the title compound were collected by filtration.

Workup

  1. customAt the end of this time, the aqueous layer was separated
  2. extractionThe oily layer was then extracted twice with a dilute hydrochloric acid solution
  3. additionsodium hydrogen carbonate was carefully added in small portions to the solution until the evolution of carbon dioxide gas
  4. extractionThe reaction mixture was then extracted with ethyl acetate
  5. concentrationthe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c3e123aeeeb143d0bf6685343b7dd4dd
Source dataset
uspto-grants-2002_05
Patent number
US06391903B1

Reaction notes

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