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

HRID 1867769노트

반응식

HRID 1867769 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8af41759ea4f44d087bbf06f2c131d3f
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632840B2

반응 노트

불러오는 중…