Water → HCID 117677449, compound

HRID 1507480Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:22][C@H:23]2[C@@H:27]3[O:28][C:29]([CH3:32])([CH3:31])[O:30][C@@H:26]3[C@@H:25]([CH2:33][OH:34])[CH2:24]2)=[N:12][C:13](S(C)(=O)=O)=[N:14][C:15]=1[O:16][CH3:17].[OH-].[NH4+:36].O>O1CCOCC1>[NH2:36][C:13]1[N:12]=[C:11]([NH:22][C@H:23]2[C@@H:27]3[O:28][C:29]([CH3:32])([CH3:31])[O:30][C@@H:26]3[C@@H:25]([CH2:33][OH:34])[CH2:24]2)[C:10]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[C:15]([O:16][CH3:17])[N:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of Compound 8 (1.36 g, 2.458 mmol) and ammonium hydroxide (25 ml, 180 mmol) in 1,4-dioxane (25 ml) was heated in a sealed tube at 80° C. for a period of 1 hr. The solution was cooled to room temperature, and water was added. The aqueous layer was extracted twice by dichloromethane and the combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum. The residue was then purified by column chromatrography on silica gel (EtOAc/hexanes) to give the title compound. 1H NMR (CDCl3) δ 10.65-10.64 (m, 1H), 7.89-7.43 (m, 2H), 7.43-7.39 (m, 1H), 7.30-7.26 (m, 1H), 4.99 (s, 2H), 4.71-4.69 (m, 1H), 4.63-4.58 (m, 2H), 4.08 (s, 3H), 3.90-3.86 (m, 2H), 2.59-2.54 (m, 1H), 2.47-2.46 (m, 1H), 2.17 (s, 1H), 1.84-1.76 (m, 2H), 1.54 (s, 3H), 1.27 (s, 3H); LCMS 2.01 min, 444 (M+H)

Workup

temperatureThe solution was cooled to room temperature
extractionThe aqueous layer was extracted twice by dichloromethane
dry with materialthe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was then purified by column chromatrography on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record: ord-cbf71489acd4402db66981aabd9978fc
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221809B2

Reaction notes

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