Water → HCID 69300184, compound

HRID 2252386Notes

Reaction equation

[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH2:10][CH2:11][C@H:12]2OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:31][CH3:32])[CH:4]=[CH:5]2.[C:33]1(=[O:43])[NH:37][C:36](=[O:38])[C:35]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:34]12.[K].O>CN(C=O)C>[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH2:10][CH2:11][C@H:12]2[N:37]2[C:33](=[O:43])[C:34]3=[CH:42][CH:41]=[CH:40][CH:39]=[C:35]3[C:36]2=[O:38])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:31][CH3:32])[CH:4]=[CH:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

In 15 mL of DMF, 321 mg (0.70 mmol) of toluene-4-sulfonic acid-(4,5α-epoxy-3-methoxy-17-methyl-morphinan-6β-yl)-ester was dissolved, and 196 mg of potassium phthalimide was added thereto, followed by stirring the mixture at 80° C. for 15 hours and then at 140° C. for 20 hours. After allowing the reaction solution to cool to room temperature, water was added to the reaction mixture and the resulting mixture was extracted with chloroform. Organic layers were combined, washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. The thus obtained crude product was purified by silica gel column chromatography to obtain 116 mg (yield: 38%) of the captioned compound.

Workup

waitat 140° C. for 20 hours
temperatureto cool to room temperature
extractionthe resulting mixture was extracted with chloroform
washwashed with saturated saline
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customto obtain a crude product
customThe thus obtained crude product
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-723b41b63286474db148670c854fab89
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320984B2

Reaction notes

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