Diisopropylethylamine → HCID 90060340, compound

Participants

Reaction Conditions

Reaction Steps

No. 5328627, 1-tert-butyl (2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(E)-8-(2-heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2-hydroxy-succinate (2.81 g, 4.47 mmol) was dissolved in N,N-dimethylformamide (70 mL) and the mixture was then cooled to 0° C. in an ice bath. No. 5328632 (ethyl (S)-2-amino-3-(4-but-2-yloxy-phenyl)-propionate hydrochloride; 1.46 g, 4.90 mmol), N,N-diisopropylethylamine (3.1 mL, 17.80 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.87 g, 4.92 mmol) were added in this order, and the mixture was then stirred at 0° C. for 1.5 hours. After quenching with a mixture of a cooled solution (14 mL) of 0.5 M potassium hydrogen sulfate and water (84 mL), the mixture was extracted with 20% ethyl acetate/n-hexane (54 mL). The aqueous layer was further extracted three times with 20% ethyl acetate/n-hexane (27 mL). The organic layers were combined, and then washed with a mixture of a saturated aqueous solution (2.8 mL) of sodium chloride and water (14 mL), and with a saturated aqueous solution (14 mL) of sodium chloride in this order. The organic layers were combined, and then dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain 3.95 g (4.53 mmol, quant.) of tert-butyl (E)-(2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate.

Provenance & Evidence