4-Methylmorpholine → HCID 54262973, 화합물

HRID 436957노트

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HRID 436957 반응식
[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

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 11783563HCID 11783563, 화합물HCID 53837274HCID 53837274, 화합물

생성물 1

HCID 54262973HCID 54262973, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
-15 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60a0cd2c0a3642a1b22a57357cfab0e7
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04028319

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