Methanol → HCID 135982353, compound

HRID 606472Notes

Reaction equation

[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:17]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH:19]=[CH:20][CH:21]=2)=[O:13])[NH:3]1.[OH-].[Na+].C1COCC1.CO>O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:17]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:19]=[CH:20][CH:21]=2)=[O:13])[NH:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 4-{[3-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)phenyl]oxy}butanoate obtained in Reference Example 43 (525 mg, 1.28 mmol), 4N aqueous sodium hydroxide solution (1.6 mL), THF (10 mL), methanol (10 mL) and water (10 mL) was stirred at 100° C. for 2 hr. The mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. Water and 1N hydrochloric acid (6.41 mL) were added to the residue, and the resulting precipitate was collected by filtration, washed with water, and dried. The obtained crude crystals were recrystallized from ethanol to give the title compound as a white powder (339 mg, 69%).

Workup

temperatureto cool to room temperature
customthe solvent was evaporated under reduced pressure
additionWater and 1N hydrochloric acid (6.41 mL) were added to the residue
filtrationthe resulting precipitate was collected by filtration
washwashed with water
customdried
customThe obtained crude crystals
customwere recrystallized from ethanol

Sources & evidence

ORD record: ord-0f399a007db1463a96aacebf1a64476c
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915267B2

Reaction notes

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