Réaction #531855

Équation de réaction

632

4-(3-Cyclohexyl-ureido)-butyric acid

1-ethyl-3-(3-(dimethylamino)-propyl) carbodiimide

tyrosine methyl ester

diisopropylethylamine

HCl

NaOH

→

target product

Rendement 18.0%

2-[4-(3-Cyclohexyl-ureido)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid

Rendement 18.0%

Solvants

DMF

acetic acid

methanol

Conditions de réaction

Traitement

1. 1
   Extractionextracted twice with a 2:1 mixture of chloroform
2. 2
   Autredried
3. 3
   Autreevaporated
4. 4
   AutreThe residue was purified by chromatography on a silica column (5×4 cm)
5. 5
   LavageElution
6. 6
   workup.ADDITIONwith a 75:25:1 mixture of ethyl acetate

Mode opératoire

To a solution of 632 (0.45 g, 2.0 mmol) and 1-ethyl-3-(3-(dimethylamino)-propyl) carbodiimide (0.5 g, 2.2 mmol) in 15 mL of DMF, 0.53 g (2.3 mmol) of tyrosine methyl ester and 2.4 mmol of diisopropylethylamine were added. The mixture was heated at 60° C. for 6 h. Then, 50 mL of 0.1 N NaOH were added and the mixture was left at room temperature overnight. The reaction mixture was then acidified with concentrated HCl and extracted twice with a 2:1 mixture of chloroform:methanol. The organic phases were pooled, dried and evaporated. The residue was purified by chromatography on a silica column (5×4 cm). Elution with a 75:25:1 mixture of ethyl acetate:methanol:acetic acid yielded 140 mg (yield: 18%) of the target product as a brown oily liquid. LC-MS-ES negative mode: 390.3 (100%, [M−H]−), 290.9 (10%, (M−C6H10N]−), 264.9 (5%, [M−C7H12NO]−); positive mode: 392.5 (40%, [M+H]+), 264.95 (100%, [M−C7H10NO]+).

Source