Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 67953455, compound

HRID 469749Notes

Reaction equation

HRID 469749 reaction equation
[CH3:1][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18]([C@@H:20]2[CH2:24][C@@H:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][N:21]2[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[O:19])[O:14][N:13]=1)([CH3:11])[CH2:3][O:4]C1CCCCO1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:4][CH2:3][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18]([C@@H:20]2[CH2:24][C@@H:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])[CH2:22][N:21]2[C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[O:19])[O:14][N:13]=1)([CH3:1])[CH3:11]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67461143HCID 67461143, compound

Product 1

HCID 67953455HCID 67953455, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2S,4R)-4-tert-Butoxy-1-(4-chloro-phenyl)-pyrrolidine-2-carboxylic acid {3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-amide (123 mg, 0.237 mmol) and pyridinium p-toluenesulfonate (20 mg, 0.047 mmol) in ethanol (2 mL) is heated at 55° C. for 42 hours. After this time, the reaction mixture is concentrated in vacuo. Purification by flash chromatography on silica gel using ethyl acetate/hexanes provides the title compound, m/z 436 [M+H+].

Workup

  1. concentrationAfter this time, the reaction mixture is concentrated in vacuo
  2. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-988387640a754a49bc2faf9405efc27f
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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