4-Methylmorpholine → HCID 54262973、化合物

HRID 436957ノート

反応式

HRID 436957 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([NH:20][CH2:21][C:22]([NH:24][C@H:25]([C:27](O)=[O:28])[CH3:26])=[O:23])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:45]([O:52][C:53](=[O:71])[C@H:54]([CH2:67][CH:68]([CH3:70])[CH3:69])[NH:55][C:56](=[O:66])[C@H:57]([CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[NH2:58])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CN(C)C=O.O>[CH2:45]([O:52][C:53](=[O:71])[C@H:54]([CH2:67][CH:68]([CH3:69])[CH3:70])[NH:55][C:56](=[O:66])[C@H:57]([CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[NH:58][C:27](=[O:28])[C@H:25]([CH3:26])[NH:24][C:22](=[O:23])[CH2:21][NH:20][C:18](=[O:19])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 11783563HCID 11783563、化合物HCID 53837274HCID 53837274、化合物

生成物 1

HCID 54262973HCID 54262973、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-15 °C

実験手順

14.0 Parts N-t-butoxycarbonyl-L-tyrosylglycyl-L-alanine and 3.5 parts N-methylmorpholine are dissolved in 200 parts dimethylformamide and cooled to -15° C. Then, 5.2 parts isobutyl chloroformate is added dropwise over a 30 minute period while maintaining the temperature at -15° C. Then, a solution of 9.8 parts L-phenylalanyl-L-leucine benzyl ester in 50 parts dimethylformamide is slowly added at -15° C., and the mixture stirred at this temperature for 30 minutes. The cooling apparatus is removed and the mixture stirred at ambient temperatures for an additional two hours. The product is isolated by diluting the reaction mixture with 10 volumes water and extracting with ethyl acetate. The ethyl acetate extracts are combined, dried over anhydrous sodium sulfate and stripped to dryness under reduced pressure. Purification of the residue by low pressure column chromatography affords N-t-butoxycarbonyl-L-tyrosylglycyl-L-alanyl-L-phenylalanyl-L-leucine benzyl ester.

後処理

  1. temperaturewhile maintaining the temperature at -15° C
  2. customThe cooling apparatus is removed
  3. stirringthe mixture stirred at ambient temperatures for an additional two hours
  4. customThe product is isolated
  5. extractionextracting with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customPurification of the residue by low pressure column chromatography

出典と根拠

ORDレコード
ord-60a0cd2c0a3642a1b22a57357cfab0e7
出典データセット
uspto-grants-1977_06
特許番号
US04028319

反応ノート

読み込み中…