Methyl iodide → Tert-butyl 3-[benzyl(methyl)amino]-3-[(methylamino)carbonyl]azetidine-1-carboxylate

HRID 1867769ノート

反応式

HRID 1867769 の反応式
[H-].[Na+].[NH2:3][C:4]([C:6]1([N:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5].[CH3:26]I>CN(C)C=O>[CH2:19]([N:17]([CH3:18])[C:6]1([C:4]([NH:3][CH3:26])=[O:5])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:7]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69048045Tert-butyl 3-(aminocarbonyl)-3-[benzyl(methyl)amino]azetidine-1-carboxylate

生成物 1

HCID 69050278Tert-butyl 3-[benzyl(methyl)amino]-3-[(methylamino)carbonyl]azetidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (60% dispersion in mineral oil) (351 mg, 8.78 mmol) was added to a solution of tert-butyl 3-(aminocarbonyl)-3-[benzyl(methyl)amino]azetidine-1-carboxylate (described in Example 74) (1.4 g, 4.39 mmol) in dimethylformamide (14 ml) at 0° C.). After 1 hour at room temperature the reaction mixture was cooled to 0° C. and methyl iodide (0.44 ml, 7.02 mmol) added dropwise. The reaction mixture was allowed to stir at room temperature overnight, evaporated and the residues purified by preparative HPLC (standard basic conditions) to give tert-butyl 3-[benzyl(methyl)amino]-3-[(methylamino)carbonyl]azetidine-1-carboxylate as a solid, (460 mg, 31%). 1H NMR Spectrum: (CDCl3) 1.45 (s, 9H), 2.23 (s, 3H), 2.87 (d, 3H), 3.56 (s, 2H), 4.05 (d, 2H), 4.20 (brs, 2H), 6.80 (brs, 1H), 7.28 (m, 3H), 7.35 (m, 2H); Mass Spectrum: (M+H)+ 334.

後処理

  1. customevaporated
  2. customthe residues purified by preparative HPLC (standard basic conditions)

出典と根拠

ORDレコード
ord-8af41759ea4f44d087bbf06f2c131d3f
出典データセット
uspto-grants-2009_12
特許番号
US07632840B2

反応ノート

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