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 1634669ノート

反応式

HRID 1634669 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-56cdd1718b4541d0b6fc28d34642f1b9
出典データセット
uspto-grants-2003_01
特許番号
US06506786B2

反応ノート

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