Triethylamine → alpha,epsilon-dicarbobenzoxy-L-lysyl-L-phenylalanine benzyl ester

HRID 354713노트

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HRID 354713 반응식
[C:1]([C@@:11]([C:28](O)=[O:29])([CH2:13][CH2:14][CH2:15][CH:16]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[NH2:17])[NH2:12])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:46]([O:53][C:54](=[O:64])[C@H:55]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[NH2:56])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH2:46]([O:53][C:54](=[O:64])[C@H:55]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[NH:56][C:28](=[O:29])[C@:11]([C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])([CH2:13][CH2:14][CH2:15][CH:16]([C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[NH2:17])[NH2:12])[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

참가 물질

8

반응물 5

HCID 8471Triethylamine2회HCID 62365Isobutyl chloroformateHCID 85570p-ToluenesulfonateHCID 736312Benzyl 3-phenyl-L-alaninateHCID 22822836alpha,epsilon-dicarbobenzoxy-L-lysine

생성물 1

HCID 22822837alpha,epsilon-dicarbobenzoxy-L-lysyl-L-phenylalanine benzyl ester

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6212Chloroform용매

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온도
0 °C

실험 절차

To a stirred solution of α,ε-dicarbobenzoxy-L-lysine (4) (96 mmol, 39.69 g), toluene (310 ml) and triethylamine (96 mmol, 9.70 g) at 0° C., was added, over a period of 15 minutes, iso-butyl chloroformate (109 mmol, 14.88 g), maintaining the temperature between -5° and 0° C. The resulting jelly-like reaction mixture was stirred for 30 minutes at 0° C. and then a slurry of L-phenylalanine benzyl ester, p-toluene sulphonate (1) (96 mmol, 40.99 g) in chloroform (470 ml) and triethylamine (96 mmol, 9.70 g) was added quickly in one portion and the clear solution was allowed to stir at ambient temperature overnight.

후처리

  1. customThe resulting jelly-like reaction mixture
  2. stirringto stir at ambient temperature overnight

출처 및 근거

ORD 기록
ord-ac60421b493c45569276741815aa824e
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04376766

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