Triethylamine → Nepsilon-Benzyloxycarbonyl-Nalpha-(tert-butoxycarbonyl)-L-lysyl-L-phenylalanyl-L-leucine ethyl ester

HRID 1684415노트

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HRID 1684415 반응식
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:29])[C@H:12]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:13][C:14](=[O:24])[C@H:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH2:16])[CH3:9].C(N(CC)CC)C.[CH2:37]([O:44][C:45]([NH:47][CH2:48][CH2:49][CH2:50][CH2:51][C@@H:52]([C:61](O)=[O:62])[NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[CH2:8]([O:10][C:11](=[O:29])[C@H:12]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:13][C:14](=[O:24])[C@H:15]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:16][C:61](=[O:62])[C@H:52]([CH2:51][CH2:50][CH2:49][CH2:48][NH:47][C:45]([O:44][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:46])[NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:58])[CH3:59])=[O:55])[CH3:9]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2724765Boc-Lys(Z)-OHHCID 67716275HCID 67716275, 화합물

생성물 1

HCID 15021173Nepsilon-Benzyloxycarbonyl-Nalpha-(tert-butoxycarbonyl)-L-lysyl-L-phenylalanyl-L-leucine ethyl ester수율 92.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a mixture of 1.68 g (4 mmol) of L-phenylalanyl-L-leucine ethyl ester trifluoroacetate, 0.56 mL (4 mmol) of triethylamine and 32 mL of chloroform were added at 0° C., first 1.52 g (4 mmol) of Nε -benzyloxycarbonyl-Nα -(tert-butoxycarbonyl)-L-lysine, and then 0.83 g (4 mmol) of dicyclohexylcarbodiimide, each being added in a single portion. The reaction mixture was warmed gradually to room temperature and then stirred overnight at that temperature. The precipitate which formed was removed by filtration. The filtrate was evaporated in vacuo and the residue was chromatographed on silica gel using 3:1 methylene chloride/ethyl acetate as eluent to give 2.48 g (92.7%) of the title compound as a white solid melting at 135°-136° C. after crystallization from a mixture of ethyl acetate and isopropyl ether. The product has the structural formula: ##STR93## as further confirmed by NMR, IR and elemental analyses.

후처리

  1. additionwere added at 0° C.
  2. customThe precipitate which formed
  3. customwas removed by filtration
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was chromatographed on silica gel using 3:1 methylene chloride/ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-cce5a8f073834a6ba5d777e0d184e20b
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639885

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