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

HRID 249571

反応式

HRID 249571 の反応式
[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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-16f92afb86334198936b5dba7e08f801
出典データセット
uspto-grants-1993_05
特許番号
US05214181

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