Diisopropylethylamine → N-[O-(3-O-Methyl-beta-L-fucopyranosyl)-4-hydroxy-phenylamino-thiocarbonyl]-alanyl-alanine

HRID 650219

反応式

HRID 650219 の反応式
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:9]([OH:11])=[O:10])[CH3:8])=[O:5])[CH3:3].CCN(C(C)C)C(C)C.[CH3:21][C@@H:22]1[O:27][C@H:26]([O:28][C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[C@@H:25]([OH:36])[C@H:24]([O:37][CH3:38])[C@@H:23]1[OH:39].[N-]=[C:41]=[S:42]>O1CCOCC1.O>[CH3:38][O:37][C@@H:24]1[C@H:23]([OH:39])[C@H:22]([CH3:21])[O:27][C@H:26]([O:28][C:29]2[CH:30]=[CH:31][C:32]([NH:35][C:41]([NH:1][C@H:2]([C:4]([NH:6][C@H:7]([C:9]([OH:11])=[O:10])[CH3:8])=[O:5])[CH3:3])=[S:42])=[CH:33][CH:34]=2)[C@H:25]1[OH:36]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 5484352L-Alanyl-L-alanineHCID 18336697p-Aminophenyl 3-o-methyl-beta-l-fucosideHCID 178418790HCID 178418790、化合物

生成物 1

HCID 131722829N-[O-(3-O-Methyl-beta-L-fucopyranosyl)-4-hydroxy-phenylamino-thiocarbonyl]-alanyl-alanine

試薬・触媒・溶媒 1

HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

160 mg (1 mmol) of alanyl-alanine are taken up in 20 ml of dioxane/water 1:1, and 1 ml of Hünig base is added. 1.2 mmol of p-aminophenyl 3-O-methyl-β-L-fucoside (Example 1.2) are first converted into the isothiocyanate in accordance with instructions 10.1.a and the product is then added to the solution of the dipeptide. The mixture is stirred at room temperature for 16 hours and the residue is purified by flash chromatography (acetonitrile/water 15:1). After concentration of the corresponding fractions, the product is precipitated from methanol/ether. Yield: 267 mg (57%).

後処理

  1. additionis added
  2. customthe residue is purified by flash chromatography (acetonitrile/water 15:1)
  3. customAfter concentration of the corresponding fractions, the product is precipitated from methanol/ether

出典と根拠

ORDレコード
ord-9102d9508e604660b95e227b259c2f80
出典データセット
uspto-grants-2001_08
特許番号
US06271342B1

関連ノート

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