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4-Methylmorpholine → Nalpha [S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteinyl]-Nepsilon-t-butoxycarbonyl-L-lysine methyl ester

HRID 249571
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HRID 249571 반응식
[CH2:1]([S:8][CH2:9][C@@H:10]([C:26](O)=[O:27])[NH:11][C:12](=[O:25])[C:13]([CH3:24])([CH3:23])[CH2:14][S:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][O:30][C:31](=[O:46])[C@H:32]([CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH2:33].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C1C=CC=CC=1.C(OCC)(=O)C>[CH3:29][O:30][C:31](=[O:46])[C@H:32]([CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:40])[NH:33][C:26](=[O:27])[C@H:10]([CH2:9][S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[NH:11][C:12](=[O:25])[C:13]([CH3:24])([CH3:23])[CH2:14][S:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7018776(S)-Methyl 2-amino-6-((tert-butoxycarbonyl)amino)hexanoateHCID 14969990S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteine

생성물 1

HCID 86746877
Nalpha [S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteinyl]-Nepsilon-t-butoxycarbonyl-L-lysine methyl ester
수율 61.1%

시약·촉매·용매 3

HCID 241Benzene용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteine (4.01 g), Nε -t-butoxycarbonyl-L-lysine methyl ester (2.08 g) and NMM (1.1 ml) in DMF (20 ml), HOBt (2.16 g) and then a solution of DCC (1.82 g) in DMF (10 ml) were added slowly under ice cooling. The mixture was stirred for 1 hr. under ice cooling and for 18 hr. at room temperature. After an addition of a mixture of ethyl acetate and benzene (2:1, 500 ml), the mixture was washed with 10% citric acid solution, water, saturated sodium bicarbonate solution, water and then saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 3.22 g (61%) of the titled compound.

후처리

  1. waitunder ice cooling and for 18 hr
  2. customat room temperature
  3. washthe mixture was washed with 10% citric acid solution, water, saturated sodium bicarbonate solution, water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by a silica gel column chromatography

출처 및 근거

ORD 기록
ord-16f92afb86334198936b5dba7e08f801
출처 데이터셋
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05214181

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