Sodium Hydroxide → Pf-06282999

HRID 75533

反応式

HRID 75533 の反応式
[NH2:1][C:2](=[O:21])[CH2:3][NH:4]/[C:5](/[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])=[CH:6]\[C:7]([O:9]CC)=O.C(OCCCC)(=O)C.C[Si]([N:34]=[C:35]=[S:36])(C)C.[OH-].[Na+]>CO.O>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]([O:19][CH3:20])=[C:12]([C:5]2[N:4]([CH2:3][C:2]([NH2:1])=[O:21])[C:35](=[S:36])[NH:34][C:7](=[O:9])[CH:6]=2)[CH:17]=1

参加物

6

反応物 4

HCID 14798Sodium Hydroxide2 回HCID 31272Butyl AcetateHCID 75297IsothiocyanatotrimethylsilaneHCID 86684671(Z)-Ethyl 3-((2-amino-2-oxoethyl)amino)-3-(5-chloro-2-methoxyphenyl)acrylate

生成物 1

HCID 71571306Pf-06282999収率 53.2%

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
30 °C

実験手順

A reaction vessel equipped with an efficient stirrer was charged with (Z)-ethyl 3-((2-amino-2-oxoethyl)amino)-3-(5-chloro-2-methoxyphenyl)acrylate (15 g, 50.2 mmol), butyl acetate (150 mL) and trimethylsilyl isothiocyanate (160.7 mmole, 21.1 g, 22.7 mL) and the mixture was heated to reflux. After 15 hours, the mixture was cooled to 30° C. and treated with 1 N aqueous sodium hydroxide (112.5 mL, 112.5 mmoles). After 30 min, the organic layer was separated and extracted with another portion of 1 N sodium hydroxide (37.5 mL, 37.5 mmoles). The combined aqueous phases were extracted twice with dichloromethane (2×45 mL), filtered, and treated with 6N HCl until a pH of 2.5 was achieved. After stirring for 1 hour, the resulting solid was isolated by vacuum filtration, resuspended in 100 mL of a 1:1 methanol-water solution, heated with stirring at 50° C. for 2 hours, and cooled to room temperature before collecting the solid by vacuum filtration, pulling dry and drying in a vacuum oven (20 mm Hg, 50° C.) for 12 hours to afford 8.7 g of the desired product as a tan solid.

後処理

  1. customA reaction vessel equipped with an efficient stirrer
  2. temperaturethe mixture was heated to reflux
  3. waitAfter 30 min
  4. customthe organic layer was separated
  5. extractionThe combined aqueous phases were extracted twice with dichloromethane (2×45 mL)
  6. filtrationfiltered
  7. additiontreated with 6N HCl until a pH of 2.5
  8. customthe resulting solid was isolated by vacuum filtration
  9. temperatureheated
  10. stirringwith stirring at 50° C. for 2 hours
  11. temperaturecooled to room temperature
  12. custombefore collecting the solid
  13. filtrationby vacuum filtration
  14. custompulling dry
  15. customdrying in a vacuum oven (20 mm Hg, 50° C.) for 12 hours

出典と根拠

ORDレコード
ord-d43b8e96baad488d821ca2326863817b
出典データセット
uspto-grants-2014_09
特許番号
US08835449B2

関連ノート

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