p-Toluenesulfonic acid → HCID 57161347, compound

HRID 1856663Notes

Reaction equation

HRID 1856663 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:19][CH2:18][C@@H:17]([NH:20][C:21]([N:23]3[C@@H:27]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=4)[C@H:26]([CH2:36][O:37]C4CCCCO4)[O:25][C:24]3=[O:44])=[O:22])[CH2:16]2)[CH2:11][CH2:10]1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:19][CH2:18][C@@H:17]([NH:20][C:21]([N:23]3[C@@H:27]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=4)[C@H:26]([CH2:36][OH:37])[O:25][C:24]3=[O:44])=[O:22])[CH2:16]2)[CH2:11][CH2:10]1)#[N:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57055185HCID 57055185, compound

Product 1

HCID 57161347HCID 57161347, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4S,5R)-4-(3,4-difluorophenyl)-2-oxo-5-(tetrahydropyran-2-yloxymethyl)oxazolidine-3-carboxylic acid {1-[1-(2-cyanophenyl)piperidin-4-yl]-(3R)-pyrrolidin-3-yl}amide (156 mg, 0.26 mmol) in methanol (5 mL) was added p-toluenesulfonic acid (50 mg, 0.26 mmol). The reaction mixture was stirred at room temperature for 17 h. The volatiles were removed under reduced pressure, the residue taken up in ethyl acetate (100 mL), washed with saturated sodium carbonate solution (3×100 mL), brine (1×100 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 {1-[1-(2-cyanophenyl)piperidin-4-yl]-(3R)-pyrrolidin-3-yl}amide. The hydrochloride salt was prepared according to standard procedures to provide a white solid (123 mg, 0.22 mmol, 84%)

Workup

  1. customThe volatiles were removed under reduced pressure
  2. washwashed with saturated sodium carbonate solution (3×100 mL), brine (1×100 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-f0db0f4af34144edbb68466ef2e87d08
Source dataset
uspto-grants-2000_11
Patent number
US06143750

Reaction notes

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