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Volumn 44, Issue 33, 2003, Pages 6339-6342

Protecting group migration in the chemistry of 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone

Author keywords

N silylation; O silylation; Silyl migration; lactam

Indexed keywords

1 TERT BUTYLDIMETHYLSILYL 4 HYDROXYMETHYL 2 AZETIDINONE; AZETIDINONE DERIVATIVE; BROMINE DERIVATIVE; CARBONYL DERIVATIVE; CHLOROFORMIC ACID ETHYL ESTER; OXIDE; UNCLASSIFIED DRUG;

EID: 18844471809     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01525-9     Document Type: Article
Times cited : (5)

References (14)
  • 11
    • 85031142861 scopus 로고    scopus 로고
    • 3NSi requires C, 63.91; H, 7.89; N, 4.38%);
    • Ar), 166.1 and 171.8 (2×C=O); m/z (EI) 319 (3), 121 (69), 105 (100) and 77 (66).
  • 12
    • 85031135471 scopus 로고    scopus 로고
    • 4, filtered and concentrated under vacuum. A solution of the deprotected β-lactam in THF (5 mL), cooled at -78°C under argon atmosphere, was dropwise added to a solution of LiHMDS (1 equiv.) in dry THF (3 mL). The mixture was stirred for 30 min at -78°C, then phenethyl chloroformate (46 mg; 0.25 mmol) was added with a syringe through a rubber stopper. Stirring was continued for 1 h at this temperature and the mixture was allowed to reach room temperature and stirred for 3 h at 20°C
    • Ar), 148.7 (CO carbamate), 163.1 and 165.9 (CO azetidinone and CO amide); m/z (CI) 354 (M+1, 4), 105 (100), 91 (12) and 77 (66).
  • 13
    • 85031136187 scopus 로고    scopus 로고
    • 4, filtered and concentrated under vacuum
    • Ar), 154.4 (CO carbonate), 166.1 (CO azetidinone); m/z (CI) 340 (M+1, 12), 298 (51) and 105 (100).
  • 14
    • 85031132811 scopus 로고    scopus 로고
    • 4, filtered and concentrated under vacuum
    • Ar), 149.1 (CO carbamate), 164.0 (CO azetidinone); m/z (CI) 364 (M+1, 12), 105 (83), 91 (100).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.