3-(Dimethylamino)acrylaldehyde → Tert-butyl 3-(1,1-dimethylethylsulfinamido)-3-(pyrimidin-2-yl)azetidine-1-carboxylate

HRID 509558노트

반응식

HRID 509558 반응식
[C:1]([C:4]1([NH:15][S:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:17])[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1)(=[NH:3])[NH2:2].C[O-].[Na+].CN(C)/[CH:27]=[CH:28]/[CH:29]=O>CO>[CH3:19][C:18]([CH3:21])([S:16]([NH:15][C:4]1([C:1]2[N:2]=[CH:29][CH:28]=[CH:27][N:3]=2)[CH2:5][N:6]([C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])[CH2:7]1)=[O:17])[CH3:20]

참가 물질

5

반응물 3

HCID 6383203-(Dimethylamino)acrylaldehydeHCID 10942334Sodium MethoxideHCID 89835483Tert-butyl 3-carbamimidoyl-3-(1,1-dimethylethylsulfinamido)azetidine-1-carboxylate

생성물 1

HCID 89825281Tert-butyl 3-(1,1-dimethylethylsulfinamido)-3-(pyrimidin-2-yl)azetidine-1-carboxylate수율 12%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
70 °C

실험 절차

To the above reaction mixture of tert-butyl 3-carbamimidoyl-3-(1,1-dimethylethylsulfinamido)azetidine-1-carboxylate (assumed 4.98 mmol) in methanol (5 mL) was added sodium methoxide (0.509 g, 9.42 mmol) and (E)-3-(dimethylamino)acrylaldehyde (0.560 g, 5.65 mmol), and the resulting solution was heated at 70° C. overnight. The reaction mixture was then concentrated and the residue dissolved in ethyl acetate. The mixture was washed with water followed by saturated brine solution, and then dried over Na2SO4 and concentrated. The crude product was then purified by column chromatography (50% EtOAc in Hexane) to afford tert-butyl 3-(1,1-dimethylethylsulfinamido)-3-(pyrimidin-2-yl)azetidine-1-carboxylate Yield: 200 mg (overall 12%). 1H NMR (400 MHz, CDCl3): δ 8.78 (d, J=4.8 Hz, 2H), 7.24 (m, 1H), 4.63-4.48 (m, 2H), 4.23 (d, J=9.2 Hz, 2H), 1.47 (s, 9H), 1.29 (s, 9H). LCMS: (ES+) m/z observed=255.2 (M+H)+ of 2-methyl-N-(3-(pyrimidin-2-yl)azetidin-3-yl)propane-2-sulfinamide.

후처리

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe mixture was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was then purified by column chromatography (50% EtOAc in Hexane)

출처 및 근거

ORD 기록
ord-ee5e53443b2e4feb84c6ce9a579fc8c4
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096580B2

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