p-Toluenesulfonic acid → HCID 9936362, compound

HRID 1976607Notes

Reaction equation

HRID 1976607 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([N:22]2[C@@H:26]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[C@H:25]([CH2:35][O:36]C3CCCCO3)[O:24][C:23]2=[O:43])=[O:21])[CH2:12][CH2:11]1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([N:22]2[C@@H:26]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[C@H:25]([CH2:35][OH:36])[O:24][C:23]2=[O:43])=[O:21])[CH2:12][CH2:11]1)#[N:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86756683HCID 86756683, compound

Product 1

HCID 9936362HCID 9936362, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4S,5R)-4-(3,4-difluorophenyl)-5-(tetrahydropyran-2-yloxymethyl)-2-oxo-oxazolidine-3-carboxylic acid {3-[4-(2-cyano-4-fluorophenyl)piperidin-1-yl]propyl}amide (122 mg, 0.20 mmol) in methanol (5 mL) was added p-toluenesulfonic acid (38 mg, 0.20 mmol). The reaction mixture was stirred at room temperature for 18 h. The volatiles were removed under reduced pressure, the residue taken up in ethyl acetate (100 mL), washed with 10% sodium carbonate solution (2×50 mL), dried over magnesium sulfate and filtered. The volatiles were removed under reduced pressure to afford (4S,5R)-4-(3,4-difluorophenyl)-5-hydroxymethyl-2-oxo-oxazolidine-3-carboxylic acid {3-[4-(2-cyano-4-fluorophenyl)piperidin-1-yl]propyl}amide. The hydrochloride salt was prepared according to standard procedures to provide a white solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. washwashed with 10% sodium carbonate solution (2×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-cb4f4d5fdc39487cbc2286098fdfdf6d
Source dataset
uspto-grants-2001_05
Patent number
US06228870B1

Reaction notes

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