Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine methyl ester → methyl (2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[(2S)-3-phenyl-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoate

HRID 396902ノート

反応式

HRID 396902 の反応式
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[N:5]([CH2:16][CH:17]([CH3:19])[CH3:18])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH2:26]1[CH2:30]O[CH2:28][CH2:27]1.[C:31]([O-:34])([O-])=O.[K+].[K+]>Cl>[CH3:28][C:27]1[CH:11]=[CH:10][C:9]([S:6]([NH:5][C@H:30]([C:31]([NH:24][CH2:23][CH2:22][CH2:21][CH2:20][C@H:4]([N:5]([S:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:16][CH:17]([CH3:18])[CH3:19])[C:3]([O:2][CH3:1])=[O:25])=[O:34])[CH2:26][C:27]2[CH:21]=[CH:20][CH:4]=[CH:3][CH:28]=2)(=[O:7])=[O:8])=[CH:30][CH:26]=1

参加物

4

反応物 2

HCID 22975548Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine methyl esterHCID 86626146potassium carbonate THF

生成物 1

HCID 508591methyl (2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[(2S)-3-phenyl-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoate収率 77%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

To a stirred solution of Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine methyl ester (369 mg, 1 mmol, example 65, step C) in THF/K2CO3 (1M) (3 mL/3 mL) was added Nα-(4-methylbenzenesulfonyl)-L-phenylalanine N-hydroxysuccinimide ester (500 mg, 1.2 mmol). The reaction mixture was stirred overnight, then diluted with 1N HCl and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated. The crude was purified by flash chromatography using hexane/EtOAc as eluent to afford the desired product (77% yield).

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude was purified by flash chromatography

出典と根拠

ORDレコード
ord-b979637fab174e1ba629c9f5ac8745f1
出典データセット
uspto-grants-2003_08
特許番号
US06608100B1

反応ノート

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