Hydrochloric Acid → HCID 11319207, compound

HRID 1180619Notes

Reaction equation

[Cl:1][C:2]1[C:25]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:24][C:5]([C:6]([O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][O:20][N+:21]([O-:23])=[O:22])[CH2:14][CH2:13]2)=[O:11])=[O:7])=[C:4]([NH:30][CH2:31][C:32]2[O:33][CH:34]=[CH:35][CH:36]=2)[CH:3]=1.Cl.CCOCC.CCCCCC>C(Cl)Cl.CCOC(C)=O.CO>[ClH:1].[Cl:1][C:2]1[C:25]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:24][C:5]([C:6]([O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][O:20][N+:21]([O-:23])=[O:22])[CH2:14][CH2:13]2)=[O:11])=[O:7])=[C:4]([NH:30][CH2:31][C:32]2[O:33][CH:34]=[CH:35][CH:36]=2)[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product of Example 5 (0.125 g, 0.23 mmol) in a mixture of CH2Cl2:EtOAc:MeOH (1:1:0.5) (5 mL) at 0° C. was added dropwise a solution of HCl gas in Et2O (0.23 mL, 8.3 mg, 1 M solution, 0.23 mmol). The cloudy solution was stirred at 0° C. for 5 minutes and hexane was added. The precipitate was filtered, washed with hexane and dried under vacuum to give the title compound (30 mg, 22% yield) as a white solid. Mp 120-125° C. (with decomposition). 1H NMR (300 MHz, d6-DMSO) δ 10.60-10.82 (br s, 1H), 8.47 (s, 1H), 8.37 (br t, J=5.6 Hz, 1H), 7.62 (s, 1H), 7.38 (s, 2H), 7.14 (s, 1H), 6.36-6.43 (m, 2H), 5.15 (br s, 2H), 4.94 (br s, 2H), 4.61 (d, J=5.6 Hz, 2H), 3.85-4.12 (m, 4H), 3.42-3.64 (m, 2H), 2.90-3.25 (m, 4H). Mass spectrum (API-TIS) m/z 546 (MH+), 568 (MNa+).

Workup

filtrationThe precipitate was filtered
washwashed with hexane
customdried under vacuum

Sources & evidence

ORD record: ord-388bbcd0651547ae97ee77b73d6d6c3b
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282519B2

Reaction notes

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