Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1975-06-30
1977-08-23
Trousof, Natalie
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
260307G, 2603322H, 260481R, C07D49504
Patent
active
040440206
ABSTRACT:
Biotin is prepared by (a) ozonizing methylcyclohexene; (b) reacting nitromethane with the methyl-6-oxohexanoate from a to form 7-nitro-6 hydroxyheptanoic acid methyl ester; (c) acylating to form the corresponding 6 acyloxy compound; (d) forming a double bond at the 6 position; (e) reacting the product of d with nitroethanethiol to form dl-7-thia-6-nitromethyl-9-nitro-nonanoic acid methyl ester; (f) forming a furoxan by cyclization; (g) reducing the furoxan and acylating to form dl-2(4-carbomethoxybutyl)-3,4-bis(acylamido)-2,5-dihydro thiophene; (h) selectively hydrogenating to form the 3,4-cis-bis(acylamido)-2,5-dihydro thiophene; and (i) hydrolyzing and cyclizing to form dl-biotin. The products formed at steps (e)-(h) are novel, as are the individual steps (e), (f), (g), and (h).
REFERENCES:
patent: 2417326 (1947-03-01), Schnider et al.
patent: 2437719 (1948-03-01), Wolf et al.
Marx Michael
Reisdorff Josef H.
Moran Tom M.
Syntex (U.S.A.) Inc.
Trousof Natalie
Walker William B.
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