Hydrochloric Acid → HCID 69001703, compound

HRID 750002Notes

Reaction equation

C([O:5][C:6](=[O:30])[CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)(C)(C)C.Cl>O1CCOCC1>[ClH:29].[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:14][C@@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13][N:8]3[CH2:7][C:6]([OH:30])=[O:5])=[CH:21][CH:20]=2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To the product from step 1 (55 mg, 0.127 mmol) in 1,4-dioxane (2 mL) was added 12N HCl (1.7 mL) and the resulting mixture was stirred at 55° C. for 5 h. The solvent was removed in vacuo to obtain the product as a solid. The oil was triturated with diethyl ether (4 mL) to obtain the title product as a white solid (27 mg, 52%): MS; m/z 374 (M−H): LCMS (UV) 94%; 1H NMR (400 MHz, DMSO-d6) δ 1.49-1.54 (m, 1H), 1.74-1.83 (m, 4H), 1.93-1.96 (m, 1H), 3.30-3.36 (m, 2H), 3.44-3.47 (m, 1H), 3.82-3.84 (m, 1H), 4.02-4.06 (m, 1H), 4.17-4.20 (m, 2H), 4.29-4.33 (dd, 1H J1=6.8 Hz, J2=10.8 Hz), 6.93-6.95 (m, 2H) 6.95-6.98 (m, 2H), 7.00-7.07 (m, 2H), 7.39-7.41 (m, 2H).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-9487b544432848bd942d905fb4959fc9
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402684B2

Reaction notes

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