Methanol → HCID 67953382, compound

HRID 469746Notes

Reaction equation

HRID 469746 reaction equation
[CH3:1][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18]([C@@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[O:19])[O:14][N:13]=1)([CH3:11])[CH2:3][O:4]C1CCCCO1.CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(#N)C>O>[OH:4][CH2:3][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18]([C@@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[O:19])[O:14][N:13]=1)([CH3:11])[CH3:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 6342AcetonitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 67953440HCID 67953440, compound

Product 1

HCID 67953382HCID 67953382, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of (S)-1-(4-Chloro-phenyl)-pyrrolidine-2-carboxylic acid {3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-amide (130 mg, 0.29 mmol) in the mixture of methanol in water (10:1, 3 mL) is added p-toluenesulfonic acid monohydrate (10 mg, 0.053 mmol) and acetonitrile (1 mL). The reaction mixture is stirred at room temperature for 18 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, ESI m/z 364 [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-8b625f72c3494934a906474a996b94f7
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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