An efficient method for the synthesis of 3-mercapto-1-(1,3-thiazolin-2-YL)Azetidine useful for the pendant moiety of oral carbapenem, L-084

Heterocycles

Volumn 68, Issue 9, 2006, Pages 1821-1824

  Isoda, Takeshi ^a   Tamai, Satoshi ^a   Kumagai, Toshio ^a   Nagao, Yoshimitsu ^b  

^a Medical Research Laboratories   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749371412     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-06-10810     Document Type: Article

References (23)

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7. Data for 5: colorless crystals (from CH30H-H20), mp 225'C (decomp.); IR (KBr) 3230, 1556, 1308, 1193, 1029 cm'; 'H NMR (400 MHz, D20) 54.19-4.27 (m, 2H), 4.44-4.54 (m, 3H); HRMS (FAB) calcd for C3H8NO3S2 169.9946 (MW+H), found m/z 169.9932 (M++H).
8. Data for 3: colorless crystals (from CH30H-H20), mp 218 °C (decmp.); IR (KBr) 3129, 3041, 1656, 1453, 1242, 1205, 1024 cm-1;'H NMR (400 MHz, CD30D) 53.65 (t, J= 7.5 Hz, 2H), 4.00 (t, J= 7.5 Hz, 2H), 4.43-4.56 (m, 3H), 4.70 (dd, J= 8.4, 9.3 Hz, 2H); HRMS (FAB) calcd for C6H11N203S3 254.9932 (MW+H), found m/z 254.9953 (M++H).
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21. HPLC conditions: Ultron VX-octyl 4.6 x 250 mm, 0.01 M sodium dodecyl sulfate (pH 2.2):MeCN = 1:1, 216 nm, rt, 1.4 ml/min.
22. Compounds (7a-d) were isolated as oils from each reaction mixture. Data for 7a: 1H NMR (400 MHz, CDC13) 52.46 (s, 3H), 3.36 (m, 2H), 3.87-3.92 (m, 1H), 3.99-4.05 (m, 4H), 4.29 (m, 2H); EI-MS m/z 220 (M). Data for 7b: 1H NMR (400 MHz, CDC13) 52.89 (dt, J= 5.9, 9.0 Hz, 2H), 3.36 (t, J = 7.7 Hz, 2H), 3.84-3.90 (m, 2H), 3.91-3.96 (m, 1 H), 3.99-4.04 (m, 4H), 4.31 (t, J = 7.7 Hz, 2H); EI-MS m/z 251 (M++H). Data for 7c: 1H NMR (400 MHz, CDC13) 5 3.33-3.38 (m, 2H), 3.83-4.04 (m, 5H), 4.22-4.32 (m, 2H), 7.20-7.54 (m, 5H); EI-MS m/z 282 (M). Data for 7d: 1H NMR (400 MHz, CDC13) 5 3.33 (t, J = 7.5 Hz, 2H), 3.39-3.46 (m, 1H), 3.81 (dd, J = 5.6, 8.7 Hz, 2H), 3.92 (s, 2H), 4.00 (t, J= 7.5 Hz, 2H), 4.07 (dd, J= 8.4, 8.7 Hz, 2H), 7.26-7.35 (m, 5H); EI-MS m/z 296 (M).
23. The Bunte salt (3) was reacted with 1-HCI in the presence of NaOMe (2 equiv.) to afford 6 in 73% isolated yield. However, it was observed that only a trace amount of 6 was formed in the reaction shown in Scheme 2.