Water → Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1383744노트

반응식

HRID 1383744 반응식
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:23]([CH3:48])[C@H:24]([C:28]([N:30]([CH3:47])[C@H:31]([C:44]([NH2:46])=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:34]=1)=[O:29])[CH:25]([CH3:27])[CH3:26].O.C(OCC)(=O)C>C1COCC1.ClC(OCC(C)C)=O.CN1CCOCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([N:23]([CH3:48])[C@H:24]([C:28]([N:30]([CH3:47])[C@H:31]([C:44]([NH2:46])=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40]([CH3:43])([CH3:41])[CH3:42])[CH:34]=1)=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 131722752N-Me-Val-N-Me-Tyr(3-tBu)-NH2

생성물 1

HCID 131722753Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

시약·촉매·용매 3

HCID 79724-Methylmorpholine용매HCID 8028Tetrahydrofuran용매2회HCID 62365Isobutyl chloroformate용매

실험 절차

To a solution of Z-Phe-OH (742 mg) in THF (3 ml), isobutyl chloroformate (0.32 ml) and NMM (0.27 ml) were added under cooling with ice and the mixture was stirred for 15 minutes. Subsequently, a solution of N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (600 mg) in THF (3 ml) was added and the mixture was stirred at room temperature for 10 hours. Water was added to the reaction mixture and extraction was effected with ethyl acetate. The extract was washed with saturated brine, dried with sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; n-hexane:acetone=3:2) to give Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 in the amount of 611 mg (58%).

후처리

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at room temperature for 10 hours
  3. washThe extract was washed with saturated brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; n-hexane:acetone=3:2)

출처 및 근거

ORD 기록
ord-e8669919cca647fb9505c605464bfc23
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255285B1

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