Hydrochloric Acid → (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionic acid

HRID 2386109ノート

反応式

HRID 2386109 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1)[C:7]([NH:9][C@H:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][C:12]([O:14]CC)=[O:13])=[O:8])([O-:3])=[O:2].O.[OH-].[Na+].Cl>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1)[C:7]([NH:9][C@H:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][C:12]([OH:14])=[O:13])=[O:8])([O-:3])=[O:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 44255974ethyl (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate

生成物 1

HCID 44255973(S)-3-(3,5-dinitrobenzamido)-3-phenylpropionic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

15.4 g of ethyl (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate from reaction a were dissolved in 100 ml of tetrahydrofuran, and the resulting solution was admixed with 50 ml of water. With vigorous stirring, the slightly cloudy reaction mixture was heated to 45° C., and the pH was adjusted to 13-13.5 with 32% aqueous sodium hydroxide solution and kept constant for the course of the reaction. After the reaction ended (HPLC monitoring >99 area % conversion), the pH of the solution was adjusted to 7-8 by adding 6 N hydrochloric acid, then the organic solvent was distilled off under reduced pressure. The aqueous solution was diluted to 350 ml with water, and the pH was adjusted to 1-2 with 6 N hydrochloric acid with vigorous stirring. The precipitated product was filtered off with suction and washed twice with water. After drying at 40° C. under reduced pressure, a yield of 13.67 g was determined. The HPLC purity was 99.8 area %.

後処理

  1. customWith vigorous stirring, the slightly cloudy reaction mixture
  2. customkept constant for the course of the reaction
  3. distillationthe organic solvent was distilled off under reduced pressure
  4. additionThe aqueous solution was diluted to 350 ml with water
  5. filtrationThe precipitated product was filtered off with suction
  6. washwashed twice with water
  7. customAfter drying at 40° C. under reduced pressure

出典と根拠

ORDレコード
ord-f898f596775d44349f1c488136e8147a
出典データセット
uspto-grants-2012_09
特許番号
US08268631B2

反応ノート

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