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

HRID 650219

반응식

HRID 650219 반응식
[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]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 5484352L-Alanyl-L-alanineHCID 18336697p-Aminophenyl 3-o-methyl-beta-l-fucosideHCID 178418790HCID 178418790, 화합물

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9102d9508e604660b95e227b259c2f80
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271342B1

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