4-Methylmorpholine → 2-(N-benzyloxycarbonyl-L-phenylalanyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid

HRID 1590812노트

반응식

HRID 1590812 반응식
ClC(OCC(C)C)=O.[CH2:9]([O:16][C:17]([NH:19][C@H:20]([C:28]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([OH:34])=O)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN1CCOCC1.[CH3:45][C:46]1[C:51]([C:52]([OH:54])=[O:53])=[C:50]([NH:55][C:56](=[O:62])[C@H:57]([CH:59]([CH3:61])[CH3:60])[NH2:58])[CH:49]=[CH:48][CH:47]=1>CN(C)C=O.O1CCCC1>[CH2:9]([O:16][C:17]([NH:19][C@H:20]([C:28]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([NH:58][C@H:57]([C:56]([NH:55][C:50]1[CH:49]=[CH:48][CH:47]=[C:46]([CH3:45])[C:51]=1[C:52]([OH:54])=[O:53])=[O:62])[CH:59]([CH3:61])[CH3:60])=[O:34])=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

7

반응물 4

HCID 79724-Methylmorpholine2회HCID 62365Isobutyl chloroformateHCID 11899094Z-Phe-pro-OHHCID 541805686-methyl-2-(L-valylamino)benzoic acid

생성물 1

HCID 543276212-(N-benzyloxycarbonyl-L-phenylalanyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid수율 57.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

Isobutyl chloroformate (0.17 ml) was added to a tetrahydrofuran solution (3.5 ml) containing N-benzyloxycarbonyl-L-phenylalanyl-L-proline (523 mg) and N-methylmorpholine (0.15 ml) at -15° C., and the mixture was stirred for 0.5 hour. An N,N-dimethylformamide solution (5.5 ml) containing 6-methyl-2-(L-valylamino)benzoic acid (220 mg) and N-methylmorpholine (0.12 ml) was added dropwise to the obtained reaction mixture at -15° C., and the mixture was stirred at this temperature for 0.5 hour and then at room temperature for two hours. The reaction mixture was treated by the same procedures as in item (c) of Example 1 to obtain 2-(N-benzyloxycarbonyl-L-phenylalanyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid (317 mg).

후처리

  1. additionwas added dropwise to the obtained reaction mixture at -15° C.
  2. stirringthe mixture was stirred at this temperature for 0.5 hour
  3. waitat room temperature for two hours

출처 및 근거

ORD 기록
ord-8a80297e57d64c4a89ee6570486caeb2
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05204462

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