Hydrochloric Acid → HCID 69001118, compound

HRID 750000Notes

Reaction equation

C[O:2][C:3](=[O:29])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1.Cl>O1CCOCC1>[ClH:28].[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@@H:8]3[CH2:9][CH2:10][CH2:11][CH2:12][N:7]3[CH2:6][CH2:5][CH2:4][C:3]([OH:29])=[O:2])=[CH:16][CH:17]=2)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To the product from Example 60 (37 mg, 0.0885 mmol) in 1,4-dioxane (1.5 mL) was added 12N HCl (1 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 product as a creamish red solid. (39 mg, 99%): MS; m/z 404 (M+H): LCMS (UV) 94%; 1H NMR (400 MHz, DMSO-d6) δ 1.54-1.57 (m, 1H), 1.80-1.96 (m, 5H), 2.32-2.36 (m, 2H), 3.12-3.22 (m, 3H), 3.37-3.41 (m, 3H), 3.60-3.64 (m, 1H), 4.25-4.35 (m, 2H), 6.94 (d, 2H, J=6.8 Hz), 7.06 (s, 4H), 7.4 (d, 2H, J=6.4 Hz), 10.15 (s, 1H), 12.3 (s, 1H).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-88ec207b75654039aec118fc76f5bf0f
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402684B2

Reaction notes

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