4-Methylmorpholine → HCID 178501375、化合物

HRID 1395813ノート

反応式

HRID 1395813 の反応式
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([OH:13])=O)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[CH3:30][O:31][C:32](=[O:64])[C@H:33]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([OH:63])=[CH:59][CH:58]=1)[NH:34][C:35](=[O:55])[C@H:36]([CH:52]([CH3:54])[CH3:53])[NH:37][C:38](=[O:51])[C@H:39]([CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:50])[NH2:49])[NH:40][N+:41]([O-:43])=[O:42]>C(Cl)Cl>[CH3:30][O:31][C:32](=[O:64])[C@H:33]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([OH:63])=[CH:59][CH:58]=1)[NH:34][C:35](=[O:55])[C@H:36]([CH:52]([CH3:54])[CH3:53])[NH:37][C:38](=[O:51])[C@H:39]([CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:49])[NH2:50])[N:40]([C:11](=[O:13])[CH2:10][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:9])[N+:41]([O-:43])=[O:42]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 178501377HCID 178501377、化合物

生成物 1

HCID 178501375HCID 178501375、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-70 °C

実験手順

8.84 g of t-butoxycarbonylsarcosine is dissolved in 200 ml of methylene chloride. 10.5 ml of N-methylmorpholine is added to the solution. The solution is cooled to -70° C. 6.1 ml of isobutyl chloroformate is then added. The reaction mixture is warmed up to -15° C. and stirred for 5 minutes. The reaction mixture is again cooled to -70° C. 25.5 g of nitroarginylvalyltyrosine methyl ester hydrochloride is added to the reaction mixture. The reaction mixture is allowed to warm to room temperature, and then is stirred for 16 hours. The reaction mixture is extracted three times with 0.5 M potassium bisulfate and once with brine. The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and stripped of solvent. The residue is dissolved in 200 ml of ethyl ether. The ether solution is added to cold rapidly stirring Skellysolve B. The white precipitate is filtered and dried to afford the product t-butoxycarbonylsarcosylnitroarginylvalyltyrosine methyl ester.

後処理

  1. temperatureThe reaction mixture is warmed up to -15° C.
  2. temperatureThe reaction mixture is again cooled to -70° C
  3. temperatureto warm to room temperature
  4. stirringis stirred for 16 hours
  5. extractionThe reaction mixture is extracted three times with 0.5 M potassium bisulfate
  6. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. dissolutionThe residue is dissolved in 200 ml of ethyl ether
  9. additionThe ether solution is added to cold rapidly stirring Skellysolve B
  10. filtrationThe white precipitate is filtered
  11. customdried

出典と根拠

ORDレコード
ord-1032476ff95445a4b3070184f5257448
出典データセット
uspto-grants-1980_05
特許番号
US04204991

反応ノート

読み込み中…