Hydrochloric Acid → HCID 51348806, compound

HRID 924845Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:18]2[NH:23][C:22](=[O:24])[NH:21][C:20]([C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:35])[O:33][CH3:34])=[CH:27][CH:26]=3)=[C:19]2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:7]=[C:8]([N+:15]([O-:17])=[O:16])[C:9]=1[O:10]C(OC)=O)[CH3:2].[OH-].[Na+].Cl.O>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:18]2[NH:23][C:22](=[O:24])[NH:21][C:20]([C:25]3[CH:26]=[CH:27][C:28]([NH:31][C:32](=[O:35])[O:33][CH3:34])=[CH:29][CH:30]=3)=[C:19]2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:7]=[C:8]([N+:15]([O-:17])=[O:16])[C:9]=1[OH:10])[CH3:2]

Participants

Conditions

Temperature: 28 °C

Procedure

To a mixture of the intermediate from Step 1 (60 mg, 0.107 mmol) in ethanol (2 mL) was added sodium hydroxide aqueous solution (2 mL, 1.25 mol/L) at 0° C., and the mixture was stirred at 28° C. for 4 h. The reaction mixture was adjusted to pH=5 with diluted hydrochloric acid. The mixture was poured into water (20 mL), and extracted with ethyl acetate (30 mL). The organic layer was washed with brine (50 mL), dried over anhydrous sodium sulfate, evaporated, and purified by preparative HPLC to give Compound 83 (24.1 mg, yield 44.6%). 1H NMR (DMSO-d6400 MHz): δ 10.28 (s, 1H), 9.70 (s, 1H), 8.64 (s, 1H), 7.51 (s, 1H), 7.44 (s, 1H), 7.32 (d, J=8.8 Hz, 2H), 7.19 (s, 1H), 7.11 (d, J=8.4 Hz, 2H), 7.07-7.00 (m, 3H), 6.84 (d, J=7.2 Hz, 2H), 5.16 (d, J=2.8 Hz, 1H), 4.06-4.01 (m, 2H), 3.65 (s, 3H), 1.35-1.31 (m, 3H); MS (ESI): m/z 505.0 [M+H]+.

Workup

extractionextracted with ethyl acetate (30 mL)
washThe organic layer was washed with brine (50 mL)
dry with materialdried over anhydrous sodium sulfate
customevaporated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-8aaa31fb0c07447eabf8ba10067b79f2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283229B2

Reaction notes

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