4-Chlorobenzoic Acid → 2-(4-Chlorobenzoylamino)-3-(2-quinolon-3-yl)propionic acid

HRID 2225341

反応式

HRID 2225341 の反応式
[NH2:1][CH:2]([CH2:6][C:7]1[C:8](=[O:17])[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([OH:5])=[O:4].C(N(CC)CC)C.P(Cl)(OCC)(OCC)=O.[Cl:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][CH:36]=1>O1CCCC1>[Cl:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([NH:1][CH:2]([CH2:6][C:7]2[C:8](=[O:17])[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:3]([OH:5])=[O:4])=[O:40])=[CH:37][CH:36]=1

参加物

6

反応物 4

HCID 63184-Chlorobenzoic AcidHCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 133420972-Amino-3-(2-quinolon-3-yl)propionic acid

生成物 1

HCID 133421032-(4-Chlorobenzoylamino)-3-(2-quinolon-3-yl)propionic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

1.2 Grams of 2-amino-3-(2-quinolon-3-yl)propionic acid and 0.8 ml of triethylamine were suspended in 10 ml of tetrahydrofuran, then under stirring condition at a room temperature, a solution containing 1.0 g of diethyl chlorophosphate in 10 ml of tetrahydrofuran was added dropwise thereto, and the reaction mixture was stirred at a room temperature for 3 hours. To this reaction mixture was added a solution containing 1.0 g of p-chlorobenzoic acid in 10 ml of tetrahydrofuran dropwise and the whole reaction mixture was further stirred at a room temperature for 10 hours. After completion of the reaction, the crystals precipitated were removed by filtration, the filtrate was concentrated and to the residue was poured a saturated sodium hydrogencarbonate aqueous solution, then extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride aqueous solution and dried with sodium sulfare. The solvent was removed by distillation and the residue was recrystallized from ethanol-water to obtain 0.9 g of 2-(4-chlorobenzoylamino)-3-(2-quinolon-3-yl)propionic acid in the form of white powder product.

後処理

  1. additionwas added dropwise
  2. stirringthe reaction mixture was stirred at a room temperature for 3 hours
  3. additionTo this reaction mixture was added a solution
  4. customthe whole reaction mixture
  5. stirringwas further stirred at a room temperature for 10 hours
  6. customAfter completion of the reaction
  7. customthe crystals precipitated
  8. customwere removed by filtration
  9. concentrationthe filtrate was concentrated and to the residue
  10. additionwas poured a saturated sodium hydrogencarbonate aqueous solution
  11. extractionextracted with chloroform
  12. washThe organic layer was washed with water
  13. dry with materiala saturated sodium chloride aqueous solution and dried with sodium sulfare
  14. customThe solvent was removed by distillation
  15. customthe residue was recrystallized from ethanol-water

出典と根拠

ORDレコード
ord-99ec18de92e04031a18330f50956821a
出典データセット
uspto-grants-1994_09
特許番号
USRE034722

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