Triethylamine → HCID 58391192, compound

To a suspension of N-methyl pipecolinic acid (0.15 mmole, 21 mg) in dichlbromethane (5 mL) were subsequently added, in the order, HOAt (0.11 mmole, 15 mg), HATU (0.11 mmole, 42 mg) and Et3N (0.21 mmole, 29 μL). After stirring for 5 minutes, a solution in dichloromethane (1 mL) of the compound obtained in example 15.3 (0.1 mmole, 46 mg) was added. The reaction mixture was stirred for 4 hours, At the end dichloromethane was removed under vacuum. The crude product was dissolved in ethyl acetate (10 mL) and washed, in the order, with a NaHCO3 saturated aqueous solution (1×10 mL) and with brine (1×10 mL). The organic phase were dried over Na2SO4, filtered and concentrated under vacuum. The product was purified by flash chromatography (eluent chloroform:methanol 97:3 volume/volume). 58 mg (99% yield) of pure 2-((1R,3R)-3-((2S,3S)-2-azido-N-(2-methoxyethyl)-3-methylpentanamido)-1-hydroxy-4-methylpentyl)-N-methylthiazole-4-carboxamide were isolated. Rf=0.37 (chloroform/methanol 97:3 volume/volume). 1HNMR (400 MHz, CDCl3) δ: 8.07 (s, 1H), 7.62 (m, 1H), 7.57 (m, 1H), 5.75 (dd, 1H), 4.61 (dd, 1H), 4.11 (m, 1H), 3.70-3.48 (m, 4H), 3.22 (s, 3H), 3, 20-3.08 (m, 1H), 2.92 (m, 3H), 2.88-2.78 (m, 1H), 2.40 (m, 1H), 2.2-2.09 (m, 6H), 2.09-1.81 (m, 5H), 1.69-1.48 (m, 5H), 1.39-1.30 (m, 1H), 1.26-1.09 (m, 1H), 1.08-0.86 (m, 12H).

1. customwas removed under vacuum
2. dissolutionThe crude product was dissolved in ethyl acetate (10 mL)
3. washwashed, in the order, with a NaHCO3 saturated aqueous solution (1×10 mL) and with brine (1×10 mL)
4. dry with materialThe organic phase were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customThe product was purified by flash chromatography (eluent chloroform:methanol 97:3 volume/volume)

ORD record

ord-f4d1c5f141114b4e8f9473ecadcb789f

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580820B2