Hydrochloric Acid → Z-PyroGlu-Pro-Arg(NO2)

HRID 1197073ノート

反応式

HRID 1197073 の反応式
Cl.[NH:2]1[CH2:23][CH2:22][CH2:21][C@H:3]1[C:4]([NH:6][C@H:7]([C:18]([OH:20])=[O:19])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:17])[NH:13][N+:14]([O-:16])=[O:15])=[O:5].[N:24]1([C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[C:28](=[O:29])[CH2:27][CH2:26][C@H:25]1[C:30](O)=[O:31]>CN(C=O)C.CC(O)=O>[N:24]1([C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[C:28](=[O:29])[CH2:27][CH2:26][C@H:25]1[C:30]([N:2]1[CH2:23][CH2:22][CH2:21][C@H:3]1[C:4]([NH:6][C@H:7]([C:18]([OH:20])=[O:19])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:17])[NH:13][N+:14]([O-:16])=[O:15])=[O:5])=[O:31]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylateHCID 178512175H-Pro-Arg(NO2)

生成物 1

HCID 178512171Z-PyroGlu-Pro-Arg(NO2)収率 53.4%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

After 2.25 g (5.0 mmols) of HCl.H-Pro-Arg(NO2)-CHA was dissolved in 10 ml (15.0 mmols) of 1.5N NEM/DMF, 1.93 g (5.0 mmols) of Z-PyroGlu-SDP was added to the solution at 0° to 5° C. The resulting mixture was reacted at room temperature for 18 hours. After completion of the reaction, the reaction solution was diluted with 300 ml of AcOH followed by washing 4 times with 100 ml of cold 5% hydrochloric acid and twice with 100 ml of saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate and decoloring with activated charcoal, the AcOEt phase was distilled under reduced pressure. The residue was recrystallized from MeOH/AcOEt/ether to give 1.86 g (53.4%) of Z-PyroGlu-Pro-Arg(NO2)-CHA.

後処理

  1. additionwas added to the solution at 0° to 5° C
  2. customThe resulting mixture was reacted at room temperature for 18 hours
  3. customAfter completion of the reaction
  4. washby washing 4 times with 100 ml of cold 5% hydrochloric acid
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe AcOEt phase was distilled under reduced pressure
  7. customThe residue was recrystallized from MeOH/AcOEt/ether

出典と根拠

ORDレコード
ord-49d03015b9294ce78b2351b73a5a2dbb
出典データセット
uspto-grants-1992_05
特許番号
US05116941

反応ノート

読み込み中…