Water → HCID 86592016、化合物

HRID 1785881ノート

反応式

HRID 1785881 の反応式
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@H:11]([N:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19](=[O:22])[CH2:20]C)[CH2:10][C@@H:9]2[CH3:29])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41].O>CN(C)C=O>[CH3:43][O:42][C:40](=[O:41])[CH:39]([NH:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@H:11]([N:18]([C:19](=[O:22])[CH3:20])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:10][C@@H:9]2[CH3:29])=[O:7])=[CH:4][CH:3]=1)[CH3:44]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 86592010HCID 86592010、化合物2 回

生成物 1

HCID 86592016HCID 86592016、化合物収率 87%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

(±)-Cis-2-{4-[4-(acetyl-phenyl-amino)-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl]-phenylamino}-propionic acid methyl ester was prepared from (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. A mixture of (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide (210 mg, 0.53 mmol), potassium carbonate (123 mg, 0.89 mmol), and methyl 2-bromopropionate (70 uL, 0.63 mmol) in dry dimethylformamide (2 mL) was heated at 100° C. for 6 h, then cooled to room temperature and stirred with 20 ml water until all of the salts dissolved. The aqueous layer was separated and was extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting oil was purified by silica gel chromatography, eluting with (97:3 methylene chloride/methanol) to afford the title compound (220 mg, 87%).

後処理

  1. temperaturecooled to room temperature
  2. dissolutiondissolved
  3. customThe aqueous layer was separated
  4. extractionwas extracted with ethyl acetate
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting oil was purified by silica gel chromatography
  10. washeluting with (97:3 methylene chloride/methanol)

出典と根拠

ORDレコード
ord-4ac644dd7a2141dea55bcae060251f8c
出典データセット
uspto-grants-2009_03
特許番号
US07504508B2

反応ノート

読み込み中…