Water → 1-(4-Methoxyphenyl)-2-(2-tert-butoxycarbonylamino-4-pyridyl)ethanone

HRID 1727345

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][CH2:17][CH2:18]CCC.[CH2:22]([Li])[CH2:23][CH2:24][CH3:25].[OH2:27].C([O:31][CH:32](C)C)(C)C>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][C:22]([C:23]2[CH:16]=[CH:17][C:18]([O:31][CH3:32])=[CH:25][CH:24]=2)=[O:27])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 2-tert-butoxycarbonylamino-4-methylpyridine (20 g, 97 mmol) in anhydrous tetrahydrofuran (300 mL) was cooled to −78° C., and to this was added dropwise a 1.6 M n-butyllithium hexane solution (140 mL, 0.23 mol) with stirring. After completion of the addition, the solution was stirred for 30 minutes at 0° C., then, the solution was cooled to −78° C. A solution of N-(4-methoxybenzoyl)propyleneimine (25 g, 0.13 mol) in anhydrous tetrahydrofuran (50 mL) was added dropwise. After completion of the addition, the reaction mixture was stirred for 2 hours at room temperature. To the reaction mixture was added water (100 mL) and isopropyl ether (300 mL), and the resulted crude crystal was filtrated. This crude crystal was recrystallized from tetrahydrofuran-hexane to obtain a title compound (23 g, yield: 69%).

Workup

additionAfter completion of the addition
stirringthe solution was stirred for 30 minutes at 0° C.
additionAfter completion of the addition
stirringthe reaction mixture was stirred for 2 hours at room temperature
customthe resulted crude crystal
filtrationwas filtrated
customThis crude crystal was recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record: ord-ed1d5cbfb8bd42cba4379ff97c1d26a6
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495018B2

Linked notes

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