Hydrochloric Acid → HCID 68611403, compound

HRID 2095372Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([O:17][CH2:18][C@@H:19]3[CH2:22][CH2:21][N:20]3C(OC(C)(C)C)=O)[CH:16]=2)[O:8][N:7]=1.[ClH:31]>CO.CCOCC>[ClH:31].[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([O:17][CH2:18][C@@H:19]3[CH2:22][CH2:21][NH:20]3)[CH:16]=2)[O:8][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-[5-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]-3-isoxazolyl]propionic acid methyl ester (100 mg, 0.24 mmol) in MeOH (34 mL) was added at 0° C. 2M anhydrous HCl in ether (12 mL). The reaction mixture was stirred at 0° C. for 7 h, then concentrated in vacuo. The residue was purified by HPLC to give the hydrochloride (90 mg). 1H NMR (CD3OD, 400 MHz) δ 8.70 (s, 1H), 8.46 (s, 1H), 7.93 (d, 1H, J=1.6 Hz), 6.93 (s, 1H), 4.92 (s, 1H), 4.49 (m, 2H), 4.10 (m, 2H), 3.69 (s, 3H), 3.04 (t, 2H, J=7.2 Hz), 2.80 (t, 2H, J=7.2 Hz), 2.70 (m, 2H). 13C NMR (CDCl3, 100 MHz) δ 174.3, 165.8, 164.6, 158.5, 134.0, 133.1, 129.5, 128.5, 105.8, 70.1, 60.3, 52.5, 45.1, 32.7, 22.6, 22.0.

Workup

concentrationconcentrated in vacuo
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-d8ffdf4ab92c4be2be4cd591c34dbff1
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445684B2

Reaction notes

Loading…