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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 52693Erstellt: 23. Oktober 2026

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ritonavir

https://huagongshe.com/de/reaction/52693

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Edukt1-Hydroxybenzotriazole hydrateHCID 2796029—
EduktUreidovalineHCID 9818282—
Edukt1,3-Thiazol-5-ylmethyl N-((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl)carbamateHCID 11101978—
LösungsmittelTetrahydrofuranHCID 8028—
ProduktRitonavirHCID 39262274,6%

Reaktionsschritte

A solution of 70 mg (0.223 mmol) of N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine, 79 mg (0.186 mmol) of (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane, 30 mg (0.223 mmol) of 1-hydroxybenzotriazole hydrate, and 51 mg (0.266 mmol) of N-ethyl-N'-dimethylaminopropyl carbodiimide in 2 ml of THF was stirred at ambient temperature for 16 h. The resulting solution was concentrated in vacuo, and the residue was purified by silica gel chromatography using 97:3 CH2Cl2 :CH3OH to provide 100 mg (74%) of the desired compound (Rf 0.4, 95:5 CH2Cl2 :CH3OH) as a solid. 1H NMR (d6 -DMSO) δ0.73 (d, J=7 Hz, 6H), 1.30 (d, J=7 Hz, 6H), 1.45 (m, 2H), 1.87 (m, 1H), 2.5-2.7 (m, 4H), 2.87 (s, 3H), 3.23 (heptet, J=7 Hz, 1H), 3.57 (m, 1H), 3.81 (m, 1H), 3.93 (m, 1H), 4.15 (m, 1H), 4.44 (AA', 2H), 4.62 (d, J=6 Hz, 1H), 5.13 (AA', 2H), 6.01 (d, J=9 Hz, 1H), 6.89 (d, J=9 Hz, 1H), 7.1-7.2 (m, 11H), 7.68 (d, J=9 Hz, 1H), 7.85 (s, 1H), 9.05 (s, 1H). Mass spectrum: (M+H)+ =721. Anal. Calcd for C37H48N6O5S2.0.5H2O: C, 60.88; H, 6.77; N, 11.51. Found: C, 60.68; H, 6.53; N, 11.36.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05616720
Quelldatensatzuspto-grants-1997_04
ORD IDord-b0b73b0700274fee9fabc3ff23f09c84
Quellennotizuspto-grants-1997_04