3,3-Diethyl-4-[4-(4-methylpiperazine-1-carbonyl)phenoxy]azetidin-2-one → HCID 22614043, compound

HRID 842428Notes

Reaction equation

HRID 842428 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:25]=[CH:24][C:13]([O:14][CH:15]3[NH:18][C:17](=[O:19])[C:16]3([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.[CH2:26]([O:33][C:34]([CH2:36][CH2:37][N:38]=[C:39]=[O:40])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:25]=[CH:24][C:13]([O:14][CH:15]3[N:18]([C:39]([NH:38][CH2:37][CH2:36][C:34]([O:33][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:35])=[O:40])[C:17](=[O:19])[C:16]3([CH2:20][CH3:21])[CH2:22][CH3:23])=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 98845843,3-Diethyl-4-[4-(4-methylpiperazine-1-carbonyl)phenoxy]azetidin-2-oneHCID 22614057Benzyl N-(oxomethylidene)-beta-alaninate

Product 1

HCID 22614043HCID 22614043, compound

Procedure

According to the method of Shrenik et al (J. Med. Chem., 35, 3745-3754 (1992)), 4-[4-[[(4-methyl)piperazin-1-yl]carbonyl]phenoxy]-3,3-diethyl-2-azetidinone, prepared as in Example 5, step F, (0.68 g, 1.97 mmol) and 2-(benzyloxycarbonyl)ethylisocyanate (0.705 g, 3.94 mmol) gave, following purification by flash column chromatography (gradient from petrol/EtOAc, 1:1 to MeOH/EtOAc, 1:9 to MeOH/EtOAc, 1:1), the title compound (840 mg, 78%) as an oil.

Workup

  1. customgave
  2. custompurification by flash column chromatography (gradient from petrol/EtOAc, 1:1 to MeOH/EtOAc, 1:9 to MeOH/EtOAc, 1:1)

Sources & evidence

ORD record
ord-a71cf482fe3a44479552fe0f2c77d17a
Source dataset
uspto-grants-2002_04
Patent number
US06375926B1

Reaction notes

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