Hydrochloric Acid → 4-[3-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid

HRID 1818594Notes

Reaction equation

Cl.C([O:4][C:5](=[O:31])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[O:17][N:16]=[C:15]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[C:22]([OH:29])[C:21]=3[Cl:30])[N:14]=2)=[CH:8][CH:7]=1)C>CCO>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:18][C:15]2[N:14]=[C:13]([CH2:12][C:9]3[CH:10]=[CH:11][C:6]([C:5]([OH:31])=[O:4])=[CH:7][CH:8]=3)[O:17][N:16]=2)=[C:21]([Cl:30])[C:22]=1[OH:29])(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 150 °C

Procedure

Add 1 N hydrochloric acid (3.6 mL) to a solution of 4-[3-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid ethyl ester (55 mg, 0.13 mmol) in EtOH (1.2 mL) in a microwave tube. Seal the tube and heat in a microwave reactor at 150° C. for 30 min. Purify the reaction mixture by reverse phase HPLC using a gradient of 90:10 to 20:80 (H2O/0.1% TFA):CCH3CN as eluent to give the title compound (17 mg, 33%). 1H NMR (DMSO-d6) δ 13.07 (s, 1H), 12.92 (s, 1H), 7.86-7.94 (m, 3H), 7.44 (d, 2H), 6.89 (d, 1H), 5.49 (s, 2H), 4.49 (s, 2H), 2.59 (s, 3H). LC-MS (m/e): 401 (M−1).

Workup

customSeal the tube
customPurify the reaction mixture by reverse phase HPLC

Sources & evidence

ORD record: ord-5a292a0b2a464189bc31d2a7a583a572
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598423B2

Reaction notes

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