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

HRID 1062645Notes

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].[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].[CH3:21][CH2:22][CH2:23]CCC.[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:16]([C:17]2[CH:21]=[CH:22][C:23]([O:31][CH3:32])=[CH:19][CH:18]=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 1.6 M n-butyllithium/hexane solution (140 mL, 0.23 mol) was added dropwise with stirring. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 min and 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 dropwise addition, the mixture was stirred at room temperature for 2 h. To the reaction mixture were added water (100 mL) and isopropyl ether (300 mL), and the obtained crude crystals were collected by filtration. The crude crystals were recrystallized from tetrahydrofuran-hexane to give the title compound (23 g, yield 69%).

Workup

additionAfter completion of the dropwise addition
stirringthe mixture was stirred at room temperature for 30 min
additionAfter completion of the dropwise addition
stirringthe mixture was stirred at room temperature for 2 h
customthe obtained crude crystals
filtrationwere collected by filtration
customThe crude crystals were recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record: ord-2e1c2879308049c4b0676845538ff3f4
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06962933B1

Reaction notes

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