Novel efficient synthesis of 1-azabicyclo[1.1.0]butane and its application to the synthesis of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol useful for the pendant moiety of an oral 1β-methyicarbapenem antibiotic L- 084

Tetrahedron Letters

Volumn 40, Issue 19, 1999, Pages 3761-3764

  Hayashi, Kazuhiko ^a,b   Sato, Chisato ^b   Hiki, Shinsuke ^a   Kumagai, Toshio ^b   Tamai, Satoshi ^b   Abe, Takao ^b   Nagao, Yoshimitsu ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b Wyeth Lederle Japan Ltd   (Japan)

Author keywords

Aza compound; Azetidines; Cyclization; Thiazolines

Indexed keywords

1 (1,3 THIAZOLIN 2 YL)AZETIDINE 3 THIOL; 1 AZABICYCLO[1.1.0]BUTANE; 1BETA METHYLCARBAPENEM; 6 (1 HYDROXYETHYL) 4 METHYL 7 OXO 3 [1 (2 THIAZOLIN 2 YL) 3 AZETIDINYL] 1 AZABICYCLO[3.2.0]HEPT 2 ENE 2 CARBOXYLIC ACID PIVALOYLOXYMETHYL ESTER; AZETIDINE DERIVATIVE; CARBAPENEM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; GRAM NEGATIVE INFECTION; PSEUDOMONAS AERUGINOSA;

NEGIBACTERIA; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA;

EID: 0033532173     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00603-6     Document Type: Article

References (25)

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15. 3OD) δ 3.38 (dd, J = 9.5, 13.9 Hz, 1 H), 3.70 (dd, J= 3.2, 13.9 Hz, 1 H), 3.94 (dd, J = 8.3, 11.0 Hz, 1 H), 4.01 (dd, J = 4.6, 11.0 Hz, 1 H), 4.52-4.60 (m, 1 H). Cf. Kimpe ND, Smaele DD, Bogaert P. Synlett. 1994, 287.
16. 3 and filtered off followed by exact adjustment to the 100 ml volume with THF. This THF solution of 1-azabicyclo[1.1.0]butane 2 was used to prepare various azetidines.
17. 9 at 0 °C under argon and then the mixture was stirred at room temperature for 18 h. The reaction mixture was analyzed by means of HPLC (ODS column, 0.05 M phosphate buffer (pH 7.0) / MeCN = 50 / 50, at 254 nm).
18. [11] The structure of 2 was optimized by using the ab initio method at the HF/6-31G* level (MacSpartan PLUS 1.1.7, Wavefunction, Inc.), which will be reported in detail elsewhere.
19. [12] n-BuLi was used for the cyclization of 4 because of the reagent's lesser expensive than PhLi.
20. 3) δ 1.86 (s, 3 H), 3.36 (s, 3 H), 4.8-5.7 (m, 5 H).
21. 3OD) δ 3.9-4.2 (m, 3 H), 4.3-4.6 (m, 2 H).
22. 3) δ 2.60 (dd, J = 8.6 Hz, 1 H), 3.60 (t, J= 7.3 Hz, 2 H), 3.9-4.2 (m, 1 H), 4.13 (t, J = 7.3 Hz, 2 H), 5.1-5.2 (m, 1 H), 12.11 (brs, 1 H).
23. 2O-MeOH, mp 80-81 °C, lit. mp 91-92 °C ; Chatterjee SS, Triggle DJ. Chem. Commun., 1968, 93.
24. [17] Cromwell NH, Phillips B. Chem. Rev. 1979, 4, 331.
25. 3OD) δ 4.26 (dd, J = 5.1, 12.4 Hz, 2 H), 4.74 (dd, J= 7.1, 12.4 Hz, 2 H), 4.8-5.0 (m, 1 H).