Diisopropylethylamine → HCID 23554371, Verbindung

A solution of L-Boc-alanine (1.57 g, 8.33 mmol), HOBt monohydrate (1.13 g, 8.33 mmol), diisopropylethylamine (1.45 mL, 8.33 mmol) and CH2Cl2 (40 mL) was purged with nitrogen and cooled in an ice bath. To the cold solution was added 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (1.60 g, 8.33 mmol) followed by a solution of 3-amino-2,3-dihydro-1-(3,3-dimethyl-2-oxobutyl)-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one (2.92 g, 8.33 mmol) dissolved in CH2Cl2 (25 mL). The cold bath was removed and the solution stirred overnight at room temperature. The reaction mixture was extracted with H2O, 0.1 N aq. citric acid, 5% aq. NaHCO3, and brine. The remaining CH2Cl2 solution was dried (MgSO4) and concentrated to a yellow foam. The title compound was isolated via column chromatography (20% EtOAc/hexanes to 60% EtOAc/hexanes) to give 4.19 g (96% yield) of light yellow foam.

1. temperaturecooled in an ice bath
2. customThe cold bath was removed
3. extractionThe reaction mixture was extracted with H2O, 0.1 N aq. citric acid, 5% aq. NaHCO3, and brine
4. dry with materialThe remaining CH2Cl2 solution was dried (MgSO4)
5. concentrationconcentrated to a yellow foam

ORD-Eintrag

ord-1eb41cc1b9f8470b83967dcbd27b32b3

Quelldatensatz

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06528505B1