4-Methylmorpholine → HCID 178455908、化合物

HRID 1395820ノート

反応式

HRID 1395820 の反応式
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([N:13]([N+:44]([O-:46])=[O:45])[C@H:14]([C:22]([NH:24][C@H:25]([C:29]([NH:31][C@H:32]([C:41](O)=[O:42])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:23])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:21])[NH2:20])=[O:12])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:48][O:49][C:50](=[O:80])[C@H:51]([CH2:78][OH:79])[NH:52][C:53](=[O:77])[C@@H:54]1[CH2:58][CH2:57][CH2:56][N:55]1[C:59](=[O:76])[C@H:60]([CH2:70][C:71]1[N:75]=[CH:74][NH:73][CH:72]=1)[NH:61][C:62](=[O:69])[C@H:63]([C@H:65]([CH2:67][CH3:68])[CH3:66])[NH2:64].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:48][O:49][C:50](=[O:80])[C@H:51]([CH2:78][OH:79])[NH:52][C:53](=[O:77])[C@@H:54]1[CH2:58][CH2:57][CH2:56][N:55]1[C:59](=[O:76])[C@H:60]([CH2:70][C:71]1[N:75]=[CH:74][NH:73][CH:72]=1)[NH:61][C:62](=[O:69])[C@H:63]([C@H:65]([CH2:67][CH3:68])[CH3:66])[NH:64][C:41](=[O:42])[C@H:32]([CH2:33][C:34]1[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=1)[NH:31][C:29](=[O:30])[C@H:25]([CH:26]([CH3:27])[CH3:28])[NH:24][C:22](=[O:23])[C@H:14]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:20])[NH2:21])[N:13]([C:11](=[O:12])[CH2:10][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:9])[N+:44]([O-:46])=[O:45]

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 178448347HCID 178448347、化合物HCID 178455960HCID 178455960、化合物

生成物 1

HCID 178455908HCID 178455908、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

9.8 g of t-butoxycarbonylsarcosylnitroarginylvalyltyrosine and 7.6 g of isoleucylhistidylprolylserine methyl ester hydrochloride are dissolved in 100 ml of dimethylformamide. The solution is cooled to 0° C. To the solution is added 2.03 g of 1-hydroxybenzotriazole, 1.7 ml of N-methylmorpholine and 4.64 g of dicyclohexylcarbodiimide. The reaction mixture is stirred for two hours at 0° C. and then is allowed to stand at 4° C. for sixteen hours. Dicyclohexylurea is filtered from the reaction mixture and is washed with acetone. 300 ml of ethyl acetate is added to the solution. The solution is extracted three times with 300 ml saturated potassium bicarbonate and two times with 300 ml of brine. The product is extracted into 300 ml of 2 M potassium bisulfate. The acidic solution is neutralized with potassium carbonate. The slightly basic aqueous solution is extracted three times with 300 ml of methylene chloride. The methylene chloride solution, which contains the product, is dried over sodium sulfate, filtered and stripped of solvent under vacuum. The residue is dissolved in 100 ml of ethyl acetate. The solution is added to 1 liter of cold rapidly stirring Skellysolve B. The white precipitate was filtered and dried under vacuum at 55° C. to afford the product t-butoxycarbonylsarcosylnitroarginylvalyltyrosylisoleucylhistidylprolylserine methyl ester.

後処理

  1. waitto stand at 4° C. for sixteen hours
  2. filtrationDicyclohexylurea is filtered from the reaction mixture
  3. washis washed with acetone
  4. addition300 ml of ethyl acetate is added to the solution
  5. extractionThe solution is extracted three times with 300 ml saturated potassium bicarbonate and two times with 300 ml of brine
  6. extractionThe product is extracted into 300 ml of 2 M potassium bisulfate
  7. extractionThe slightly basic aqueous solution is extracted three times with 300 ml of methylene chloride
  8. dry with materialis dried over sodium sulfate
  9. filtrationfiltered
  10. dissolutionThe residue is dissolved in 100 ml of ethyl acetate
  11. additionThe solution is added to 1 liter of cold rapidly stirring Skellysolve B
  12. filtrationThe white precipitate was filtered
  13. customdried under vacuum at 55° C.

出典と根拠

ORDレコード
ord-21b1fe57ae10476f8dda479560f9be6b
出典データセット
uspto-grants-1980_05
特許番号
US04204991

反応ノート

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