Hydrochloric Acid → HCID 51348806, compound

HRID 2177939Notes

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-c41aa98cc8314457a91512b5e720e4a9
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067893B2

Reaction notes

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