Reacción #1767748

Ecuación de reacción

methyl glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride

N-methylmorpholine

isobutylchloroformate

N-methyl morpholine

Boc-D-methionine

→

methyl Boc-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate

Disolventes

ethyl acetate

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat -20° C
2. 2
   workup.WAITto stand overnight
3. 3
   OtroThe ethyl acetate layer is collected
4. 4
   Lavadowashed with water
5. 5
   Secadodried over magnesium sulfate
6. 6
   FiltraciónThe solution is filtered
7. 7
   Otrothe solvent removed under reduced pressure
8. 8
   OtroPurification of the residue by low pressure chromatography on silica gel

Procedimiento

A mixed anhydride is prepared by reacting 2.0 g of Boc-D-methionine with 0.90 ml of N-methylmorpholine and 1.06 ml isobutylchloroformate in 15 ml of tetrahydrofuran at -20° C. A solution of 2.84 g of methyl glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride in 15 ml tetrahydrofuran is neutralized with 0.78 ml N-methyl morpholine and added to the mixed anhydride reaction above. The reaction mixture is stirred for 2 hours at room temperature and allowed to stand overnight. The reaction mixture is diluted with 200 ml of ethyl acetate. The ethyl acetate layer is collected and washed with water, followed by washes with 0.2 M potassium bisulfate, water, and 1 M potassium bicarbonate and dried over magnesium sulfate. The solution is filtered and the solvent removed under reduced pressure. Purification of the residue by low pressure chromatography on silica gel affords methyl Boc-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate which is represented by the following formula ##STR17##

Fuente