Triethylamine → (+/-)-[[[2,6-Bis(1-methylethyl)phenyl]amino]2-oxoethyl]-(phenylmethyl)phosphoramidic Acid, Nonyl Phenyl Ester

To an ice-cooled solution of phenyl dichlorophosphate (2.83 g, 0.02 mol) in dry toluene (50 mL) is added triethylamine (2.02 g, 0.02 mol) followed by nonyl alcohol (2.89 g, 0.02 mol) in dry toluene (40 mL) dropwise. The reaction mixture is stirred in an ice bath for 2 hours and then filtered. To this filtrate are added triethylamine (2.02 g, 0.02 mol) and a solution of N-[2,6-bis(1-methylethyl)phenyl]-2-[phenylmethyl]amino-acetamide (Example V) (6.40 g, 0.02 mole) and the mixture is stirred at room temperature overnight. The reaction mixture is filtered and concentrated. Flash column chromatography and crystallization from ethyl acetate affords 3.8 g of the title compound; IR (KBr); 3285, 2961, 2925, 2858, 2367, 1684, and 1508. 1H NMR (250 MHz, DMSO)δ9.22 (1 H, s), 7.44-6.92 (13 H, m), 4.50-4.30 (2 H, m), 4.30-4.00 (2 H, m), 4.00-3.60 (2 H, m), 3.10-2.80 (2 H, m), 1.70-1.40 (2 H, m), 1.4-1.18 (12 H, m), 1.18-1.00 (12 H, d, J=7 Hz), 0.98-0.76 (3 H, m).

1. filtrationfiltered
2. filtrationThe reaction mixture is filtered
3. concentrationconcentrated
4. customFlash column chromatography and crystallization from ethyl acetate

ORD 기록

ord-4686ccefd43947c99c2937b26ae79b6f

출처 데이터셋

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05208224