Degradative rearrangements of N-(t-butyloxycarbonyl)-O-methanesulfonyl- hydroxamic acids: A novel, reagent-based alternative to the Lossen rearrangement

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 10040-10044

  Stafford, Jeffrey A ^a   Gonzales, Stephen S ^a   Barrett, David G ^a   Suh, Edward M ^a   Feldman, Paul L ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; N (TERT BUTYLOXYCARBONYL) O METHANESULFONYLHYDROXAMIC ACID; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; DEGRADATION; REACTION ANALYSIS;

EID: 0032567511     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981498e     Document Type: Article

References (23)

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11. Alternative strategies to provide stepwise control of the Lossen rearrangement have been reported: (a) Miller, M. J.; Loudon, G. M. J. Am. Chem. Soc. 1975, 97, 5295. (b) King, F. D.; Pike, S.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1978, 351.
12. While reagent 4 can be readily manipulated on the benchtop in open air, it is recommended that 4 be stored under nitrogen at 4°C. When stored in this manner, 4 is stable and can be used for several months. (CAUTION: Formation of hazardous peroxides of diisopropyl ether has been reported. For a review on controlling the hazards associated with peroxidized ethers see: Jackson, H. L. et al. J. Chem. Educ. 1970, 47, A175.)
13. Activation and coupling of 1 via formation of a mixed anhydride also provides good yields of 6. This method was applied for the synthesis of 9 and 11 (vide infra). Attempts at carbodiimide-based coupling procedures (e.g., EDC) were unsuccessful.
14. The use of methylene chloride or THF for the coupling of 4 to activated carboxylic acid derivatives resulted in significantly diminished yields of coupled product.
15. The alloc- and teoc-protected amines derived from these experiments, compounds Tb and 7c, respectively, are described in the Experimental Section.
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19. For comparison purposes the rearrangement of 9 in the presence of zinc triflate and benzyl alcohol provided 14a in 69% yield.
20. 2; flow rate: 2.0 mL/min; monitored at 255 nM).
21. March, J. Advanced Organic Chemistry, John Wiley & Sons: New York, 1985; Chapter 18, pp 982-987.
22. 13C NMR spectra were measured using either a Varian Unity Plus 300 or a Varian Unity Plus 400 spectrometer. Chemical shifts are expressed in ppm downfield from the internal standard, tetramethylsilane. Apparent multiplicities are designated as follows: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; or b, broad. J values are reported in Hertz. IR spectra were recorded on a Nicolet 510 FT-IR spectrometer. Mass spectra were taken in positive-ion mode by atmospheric pressure chemical ionization (APCI). Melting points were determined on a Laboratory Devices Mel-Temp III and are uncorrected. Elemental analyses were performed by Atlantic Microlab (Norcross, GA).
23. Schmid, G. H.; Wolkoff, A. W. J. Org. Chem. 1967, 32, 254.