Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 67953418, compound

HRID 469744Notes

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][C:22](=[O:25])[N:21]2[C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)=[O:19])[O:14][N:13]=1)([CH3:11])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[CH3:11][C:2]([C:12]1[CH:16]=[C:15]([NH:17][C:18]([C@@H:20]2[CH2:24][CH2:23][C:22](=[O:25])[N:21]2[C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:30][CH:31]=2)=[O:19])[O:14][N:13]=1)([CH3:1])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.[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][C:22](=[O:25])[N:21]2[C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=2)=[O:19])[O:14][N:13]=1)([CH3:11])[CH3:1]

Participants

Conditions

Temperature: 55 °C

Procedure

(S)-5-Oxo-1-(4-trifluoromethyl-phenyl)-pyrrolidine-2-carboxylic acid {3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-amide is synthesized in a similar manner as Example 16, Method 7. (S)-5-Oxo-1-(4-trifluoromethyl-phenyl)-pyrrolidine-2-carboxylic acid {3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-amide (0.546 g; 1.103 mmol) is dissolved in 2 mL ethanol and pyridinium p-toluenesulfonate (0.055 g; 0.221 mmol) is added. The mixture is heated at 55° C. for 4 h and then concentrated and purified by reverse phase HPLC to afford title compound. ESI m/z 412 [M+H]+

Workup

concentrationconcentrated
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-c307b4b5efc34d149ca8500540b44562
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629157B2

Reaction notes

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