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Efavirenz
  • Synonyms: DMP-266, L-743726
  • ATC: J05AG03
  • Use: Lorem  Lorem  Lorem 
  • Chemical name: Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam
  • Formula: Lorem ipsum dolor sit amet,
  • MW:315.68 g/mol
  • CAS-RN:154598-52-4
  • InChI Key:XPOQHMRABVBWPR-ZDUSSCGKSA-N
  • InChI:InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1

Derivatives

    (R)-enantiomer

  • Formula: C14H9ClF3NO2
  • MW:315.68 g/mol
  • CAS-RN:154801-74-8

    racemate

  • Formula: C14H9ClF3NO2
  • MW:315.68 g/mol
  • CAS-RN:177530-93-7

Substance Classes

Synthesis Path
















Substances Referenced in Synthesis Path

CAS-RN Formula Chemical Name CAS Index Name
209414-27-7 C13H11ClF3NO (αS)-2-amino-5-chloro-α-(cyclopropylethynyl)-α-(trifluoromethyl)benzenemethanol Benzenemethanol, 2-amino-5-chloro-α-(cyclopropylethynyl)-α-(trifluoromethyl)-, (αS)-
168834-43-3 C13H11ClF3NO (±)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluoro-3-butyn-2-ol Benzenemethanol, 2-amino-5-chloro-α-(cyclopropylethynyl)-α-(trifluoromethyl)-
764631-94-9 C8H7ClF3NO2 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoro-1,1-ethanediol
530-62-1 C7H6N4O 1,1'-carbonyldiimidazole 1H-Imidazole, 1,1'-carbonylbis-
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem

Trade Names

Country Trade Name Vendor Annotation
D Lorem Lorem ,1999
F Lorem Lorem
GB Lorem Lorem
I Lorem Lorem
J Lorem Lorem
USA Lorem Lorem comb.
Lorem Lorem ,1998
(wfm = withdrawn from market)

Formulations

  • Loremipsumdolorsitamet,consetetursadipscing

References

    • Radesca, L.A. et al.: Synth. Commun. (SYNCAV) 27, 24, 4373-4384 (1997).
    • a Thompson, A.S. et al.: Tetrahedron Lett. (TELEAY) 36, 49, 8937-8940 (1995).
    •  Thompson, A.S. et al.: J. Am. Chem. Soc. (JACSAT) 120, 2028-2038 (1998).
    •  Pierce, M.E. et al.: J. Org. Chem. (JOCEAH) 63, 23, 8536-8543 (1998).
    •  Choudhury, A. et al.: Org. Process Res. Dev. (OPRDFK) 7, 324-328 (2003).
    • US 9 999 999 (Merck & Co.; 21.5.1996; appl. 2.6.1995; prior. 7.8.1992, 27.4.1993).
    • US 9 999 999 (Merck & Co.; 2.9.1997; appl. 2.6.1995; USA-prior. 7.8.1992, 27.4.1993).
    • US 9 999 999 (Merck & Co.; 22.9.1998; appl. 12.3.1997; USA-prior. 7.8.1992, 27.4.1993, 28.1.1994, 2.6.1995).
    • EP 999 999 (Merck & Co.; appl. 3.8.1993; USA-prior. 7.8.1992, 27.4.1993).
    • WO 9 999 999 (Merck & Co.; appl. 24.1.1995; USA-prior. 28.1.1994).
    • WO 9 999 999 (Merck & Co.; appl. 9.2.1998; USA-prior. 12.2.1997).
    • WO 9 999 999 (Du Pont; appl. 2.4.1998; USA-prior. 7.4.1997).
    •  US 9 999 999 (Merck & Co.; 27.5.1997; appl. 25.5.1995).
    •  US 9 999 999 (Merck & Co.; 16.12.1997; USA-prior. 25.5.1995, 15.5.1996).
    •  WO 9 999 999 (Merck & Co.; appl. 21.5.1996; USA-prior. 25.5.1995).

  • synthesis of cyclopropylacetylene:

    • b Tan, L. et al.: Angew. Chem. (ANCEAD) 111, 5, 724 (1999).
    •  Grabowski, E.J.J.: Chirality (CHRLEP) 17, 249-259 (2005).
    • aa US 9 999 999 (Merck & Co.; 2.9.1997; appl. 23.1.1995).
    •  WO 9 999 999 (Merck & Co.; appl. 19.1.1996; USA-prior. 23.1.1995).
    •  WO 9 999 999 (Du Pont Merck; appl. 15.12.1997; USA-prior. 16.12.1996).
    •  US 9 999 999 (Lonza; 14.12.1999; CH-prior. 10.12.1997).
    •  US 9 999 999 (Wiley Organics; 14.9.1999; appl. 13.3.1998).

  • new syntheses:

    • Wang, Z. et al.: J. Org. Chem. (JOCEAH) 64, 6918 (1999).
    • Wang, Z. et al.: J. Org. Chem. (JOCEAH) 65, 1889 (2000).

  • process for the crystallization using an anti-solvent:

    • WO 9 999 999 (Merck & Co.; appl. 2.2.1998; USA-prior. 5.2.1997).

  • antiviral combinations:

    • WO 9 999 999 (Triangle Pharm.; appl. 7.4.1998; USA-prior. 7.4.1997).
    • WO 9 999 999 (Glaxo; appl. 14.5.1998; GB-prior. 17.5.1997).

  • enantioselective construction of a chiral efavirenz intermediate via alkynylation of a cyclic N-acyl ketimine:

    • Jiang, B.; Si, Y.-G.: Angew. Chem. (ANCEAD), 116, 218 (2004).
    • The Merck Index, 13th Ed., 3552, p. 621.
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