Carbamimidic acid, methyl ester, sulfate (1:1) → HCID 178498444、化合物

HRID 565212

反応式

HRID 565212 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:15](=O)[CH3:16])[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].S(O)(O)(=O)=O.[CH3:23][O:24][C:25](=[NH:27])[NH2:26].C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[NH:27][C:25]([O:24][CH3:23])=[N:26][C:15]([CH3:16])=[C:10]2[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

参加物

6

反応物 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 54038767HCID 54038767、化合物

生成物 1

HCID 178498444HCID 178498444、化合物収率 35.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A mixture of methyl 2-{(3,4-difluorophenyl) methylene}-3-oxobutyrate (8.8 .g, 36.6 mmol), O-methylisourea hydrogen sulfate (9.4 g, 55 mmol), and NaHCO3 (12.3 g, 0.146 mol) in DMF (30 mL) was stirred and heated at 70° C. for 16 hours. The mixture was cooled, diluted with EtOAc (300 mL) and washed with water (5×300 mL), brine (300 mL), and dried (MgSO4). Solvent was evaporated and the crude product was purified by flash column chromatography on silica gel using 10% through 20% EtOAc in hexane as the gradient eluent, to leave the product as an oil (3.82 g, 30.2%)

後処理

  1. temperatureThe mixture was cooled
  2. washwashed with water (5×300 mL), brine (300 mL)
  3. dry with materialdried (MgSO4)
  4. customSolvent was evaporated
  5. customthe crude product was purified by flash column chromatography on silica gel using 10% through 20% EtOAc in hexane as the gradient eluent

出典と根拠

ORDレコード
ord-2b9f5b52af624c5e88d7c5cb83a00e22
出典データセット
uspto-grants-2001_01
特許番号
US06172066B2

関連ノート

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