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

HRID 650219

Reaction equation

HRID 650219 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-9102d9508e604660b95e227b259c2f80
Source dataset
uspto-grants-2001_08
Patent number
US06271342B1

Linked notes

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