Diisopropylethylamine → (s)-5-(2-Hydroxy-benzoylamino)-1-methyl-1h-indole-2-carboxylic acid {2-[benzyl(methyl)amino]-2-oxo-1-phenylethyl}-amide

Temperatur

0 °C

The product of step (b) (1.36 g, 4.38 mM), PyBrOP (2.45 g, 5.26 mM), and (S)-N-benzyl-N-methyl-2-phenylglycinamide (1.91 g, 6.57 mM) were placed in a 50 mL round bottom flask. DMF (20 mL) was added and the mixture was cooled to 0° C. and treated with diisopropyl ethylamine (3 mL, 17.52 mM). After the addition was complete the cooling bath was removed and the reaction mixture was stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate (120 mL) and the mixture was washed with 1 N HCl (20 mL), water (20 mL) and brine (20 mL). The ethyl acetate was dried with MgSO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 5% diethyl ether in CH2Cl2.

1. additionAfter the addition
2. customwas removed
3. additionThe mixture was diluted with ethyl acetate (120 mL)
4. washthe mixture was washed with 1 N HCl (20 mL), water (20 mL) and brine (20 mL)
5. dry with materialThe ethyl acetate was dried with MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by flash column chromatography on silica gel eluting with 5% diethyl ether in CH2Cl2

ORD-Eintrag

ord-d659cf6d0d024d09aee99c1fc9d727ed

Quelldatensatz

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06720351B2