A practical synthesis of nelfinavir, an HIV-protease inhibitor, using a novel chiral C4 building block: (5R,6S)-2,2-dimethyl-5-hydroxy-1,3-dioxepan- 6-ylammonium acetate

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7582-7583

  Inaba, Takashi ^a   Birchler, Angela G ^b   Yamada, Yasuki ^a   Sagawa, Shoichi ^a   Yokota, Katsuyuki ^a   Ando, Koji ^a   Uchida, Itsuo ^a  

^a JAPAN TOBACCO INC   (Japan)

^b AGOURON PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2 DIMETHYL 5 HYDROXY 1,3 DIOXEPAN 6 YLAMMONIUM ACETIC ACID; AMMONIUM DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; NELFINAVIR; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0032582733     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981472n     Document Type: Article

References (16)

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5. See the Experimental Section in the Supporting Information.
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8. 2/MeCN in place of m-CPBA, which was used in the reported method. The detailed procedure is shown in the Supporting Information.
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11. 25D +96.2 (c 1.00, MeOH)) was determined by X-ray crystallographic analysis (see the Supporting Information). The atomic coordinates have been deposited with CCDC (Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK).
12. 25D +29.6 (c 1.05, MeOH). See the Supporting Information.
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15. The structure of 16 was confirmed by X-ray crystallographic analysis of diacetate 17 derived from 16 (see the Supporting Information). The atomic coordinates have been deposited with CCDC.
16. + bonds in 14 to form 1 and 16. No byproduct other than 16 was detected in the reactions listed in Table 1 (HPLC).