Water → HCID 10286026, compound

HRID 2246990Notes

Reaction equation

C([N:4]1[CH2:17][C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH:10]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:9]2[CH2:8][N:7]3[CH2:6][CH2:5]1)(=O)C.[OH-].[K+].O>CO>[CH:12]1[CH:13]=[CH:14][C:15]2[CH2:17][NH:4][CH2:5][CH2:6][N:7]3[C:16]=2[C:11]=1[CH:10]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:9]1[CH2:8]3

Participants

Conditions

Temperature: 100 °C

Procedure

The compound from example 7 (0.5 g, 1.67 mmol) was dissolved in methanol (5 mL). To the mixture was added KOH (0.99 g and 16.7 mmol) and water (5 mL). The reaction mixture was heated to 100° C. and held for 4 hours. Methanol was then added (10 mL) and the mixture was held for an additional 20 hours (16 mL). At 24 hours, KOH (0.47 g, 8.3 mmol) and methanol (16 mL) were added. After 48 hours, the reaction mixture was cooled to room temperature. The methanol was removed, and the reaction mixture was transferred to separatory funnel with methylene chloride and water. The reaction mixture was extracted with methylene chloride (3×). The combined extracts were dried with magnesium sulfate, filtered and concentrated to dryness to give 430 mg of yellow oil. Further purification (20% ammonia(2M solution in ethanol)/ethyl acetate) yielded 0.273 g of desired product (63%).

Workup

waitthe mixture was held for an additional 20 hours
waitAt 24 hours
waitAfter 48 hours
temperaturethe reaction mixture was cooled to room temperature
customThe methanol was removed
customthe reaction mixture was transferred to separatory funnel with methylene chloride and water
extractionThe reaction mixture was extracted with methylene chloride (3×)
dry with materialThe combined extracts were dried with magnesium sulfate
filtrationfiltered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-a893c404156846d19866b9586a65e70e
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687620B2

Reaction notes

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