Chloroacetaldehyde → HCID 57610917, 화합물

HRID 1873917

반응식

HRID 1873917 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[C:18](=[O:27])[C@@H:19]([NH:23][C:24]([NH2:26])=[S:25])[CH:20]([CH3:22])[CH3:21])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:29][CH:30]=O>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[C:18](=[O:27])[C@@H:19]([NH:23][C:24]3[S:25][CH:29]=[CH:30][N:26]=3)[CH:20]([CH3:21])[CH3:22])=[N:10][CH:9]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 33Chloroacetaldehyde2회HCID 576109411-((S)-1-((S)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)thiourea

생성물 1

HCID 57610917HCID 57610917, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

A solution of 1-((S)-1-((S)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)thiourea (1.29 g, 2.86 mmol) was dissolved in EtOH (50 mL) and 2-chloroacetaldehyde (0.4 mL, 3.15 mmol) was added. The mixture was heated at 70° C. overnight. A further portion of 2-chloroacetaldehyde (0.4 mL, 3.15 mmol) was added and heating continued for a further 12 h. The solution was concentrated in vacuo and the residue was purified by column chromatography (biotage), eluting with 50% EtOAc in hexanes and then 10% MeOH in EtOAc. The desired product was isolated as a orange-brown foam (557.2 mg). LCMS (NH4OAc) shows this to be of sufficient purity. Eluting further with 100% MeOH gave a second fraction (980.8 mg) which was shown to contain the product by TLC (5:4.5:0.5 hex:EtOAc:MeOH). This second fraction from the column was re-purified to give a light orange-brown foam (426.6 mg). The two fractions were combined to afford the title compound as a orange brown foam (983.8 mg, 72%).

후처리

  1. temperatureheating
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was purified by column chromatography (biotage)
  4. washeluting with 50% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-8d97429626434a32839d55f3b2be750b
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08303944B2

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