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Volumn 63, Issue 23, 1998, Pages 8536-8543

Practical asymmetric synthesis of Efavirenz (DMP 266), an HIV-1 reverse transcriptase inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLOROANILINE; DIDANOSINE; EFAVIRENZ; LAMIVUDINE; PROTEINASE INHIBITOR; RNA DIRECTED DNA POLYMERASE INHIBITOR; STAVUDINE; ZALCITABINE; ZIDOVUDINE;

EID: 15644370082     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981170l     Document Type: Article
Times cited : (226)

References (33)
  • 3
  • 6
    • 15644376567 scopus 로고    scopus 로고
    • Durable Clinical Anti-HIV-1 Activity and Tolerability for efavirenz in Combination with Indinavir (IDV) at 24 Weeks
    • Toronto
    • Mayers, D.; Riddler, S.; Bach, M.; Stein, D.; Havlir, M. D.; Kahn, J.; Ruiz, N.; Labriola, D. F.; and the efavirenz clinical development team. Durable Clinical Anti-HIV-1 Activity and Tolerability for efavirenz in Combination with Indinavir (IDV) at 24 Weeks. Clinical data presented at the ICAAC meeting, Toronto, 1997, I-175.
    • (1997) ICAAC Meeting
    • Mayers, D.1    Riddler, S.2    Bach, M.3    Stein, D.4    Havlir, M.D.5    Kahn, J.6    Ruiz, N.7    Labriola, D.F.8
  • 21
    • 15644371772 scopus 로고
    • 3 as a base was reported to give pyrrolidyl derivatives in moderate yields. Moffett, R. B. J. Org. Chem. 1949, 14, 2.
    • (1949) J. Org. Chem. , vol.14 , pp. 2
    • Moffett, R.B.1
  • 22
    • 15644367252 scopus 로고    scopus 로고
    • This simple and efficient alkylation procedure has now been used to prepare a wide variety of N,N-cycloalkyl derivatives of amino alcohols
    • This simple and efficient alkylation procedure has now been used to prepare a wide variety of N,N-cycloalkyl derivatives of amino alcohols.
  • 28
    • 15644366742 scopus 로고    scopus 로고
    • The reaction may alternately be quenched into 2 N aqueous HCl without loss of 2a into the aqueous phase. Aqueous HCl may also be used interchangeably with citric acid in purifying and recycling the ligand 5b
    • The reaction may alternately be quenched into 2 N aqueous HCl without loss of 2a into the aqueous phase. Aqueous HCl may also be used interchangeably with citric acid in purifying and recycling the ligand 5b.
  • 29
    • 15644365107 scopus 로고    scopus 로고
    • The product 2a readily upgrades in optical purity upon crystallization
    • The product 2a readily upgrades in optical purity upon crystallization.
  • 30
    • 15644366289 scopus 로고    scopus 로고
    • The less expensive quinone chloranil was also used for the deprotection step. However, the initial oxidation of 2a to give the cyclic aminals 13a/13b is not as efficient as the reaction involving DDQ, and aminals 13a/13b required purification (by crystallization) prior to conversion into the amino alcohol 2b. The isolated yield of 2b from this two-step procedure was 75-80%
    • The less expensive quinone chloranil was also used for the deprotection step. However, the initial oxidation of 2a to give the cyclic aminals 13a/13b is not as efficient as the reaction involving DDQ, and aminals 13a/13b required purification (by crystallization) prior to conversion into the amino alcohol 2b. The isolated yield of 2b from this two-step procedure was 75-80%.
  • 31
    • 0000096274 scopus 로고
    • The structure of 13b was determined by comprehensive heteronuclear NOE (HOESY) experiments. Yu, C.; Levy, G. C. J. Am. Chem. Soc. 1984, 106, 6533.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 6533
    • Yu, C.1    Levy, G.C.2
  • 33
    • 15644374100 scopus 로고    scopus 로고
    • 3 ensures pH < 8.5 and complete formation of the carbamate 14b before addition of KOH to effect ring closure
    • 3 ensures pH < 8.5 and complete formation of the carbamate 14b before addition of KOH to effect ring closure.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.