US 12,103,928 B2
Processes for preparing a diazabicyclooctane compound
Takao Abe, Kanagawa (JP); Takeshi Furuuchi, Kanagawa (JP); and Yoshiaki Sakamaki, Kanagawa (JP)
Assigned to MEIJI SEIKA PHARMA CO., LTD., Tokyo (JP)
Filed by MEIJI SEIKA PHARMA CO., LTD., Tokyo (JP)
Filed on May 18, 2023, as Appl. No. 18/199,019.
Application 18/199,019 is a division of application No. 17/399,618, filed on Aug. 11, 2021, granted, now 11,731,971.
Application 17/399,618 is a division of application No. 16/660,682, filed on Oct. 22, 2019, granted, now 11,117,896, issued on Sep. 14, 2021.
Application 16/660,682 is a division of application No. 15/973,861, filed on May 8, 2018, granted, now 10,556,905, issued on Feb. 11, 2020.
Application 15/973,861 is a division of application No. 15/583,238, filed on May 1, 2017, granted, now 10,023,573, issued on Jul. 17, 2018.
Application 15/583,238 is a division of application No. 14/872,988, filed on Oct. 1, 2015, granted, now 9,708,320, issued on Jul. 18, 2017.
Application 14/872,988 is a division of application No. 14/404,288, granted, now 9,181,250, issued on Nov. 10, 2015, previously published as PCT/JP2013/064971, filed on May 30, 2013.
Claims priority of application No. 2012-122603 (JP), filed on May 30, 2012.
Prior Publication US 2023/0331724 A1, Oct. 19, 2023
Int. Cl. C07D 471/08 (2006.01); A61K 31/407 (2006.01); A61K 31/4162 (2006.01); A61K 31/427 (2006.01); A61K 31/43 (2006.01); A61K 31/437 (2006.01); A61K 31/439 (2006.01); A61K 31/444 (2006.01); A61K 31/4545 (2006.01); A61K 31/5377 (2006.01); A61K 31/545 (2006.01); A61K 31/546 (2006.01); A61K 45/06 (2006.01); C07D 211/60 (2006.01); C07F 7/08 (2006.01)
CPC C07D 471/08 (2013.01) [A61K 31/407 (2013.01); A61K 31/4162 (2013.01); A61K 31/427 (2013.01); A61K 31/43 (2013.01); A61K 31/437 (2013.01); A61K 31/439 (2013.01); A61K 31/444 (2013.01); A61K 31/4545 (2013.01); A61K 31/5377 (2013.01); A61K 31/545 (2013.01); A61K 31/546 (2013.01); A61K 45/06 (2013.01); C07D 211/60 (2013.01); C07F 7/0812 (2013.01); Y02P 20/55 (2015.11)] 9 Claims
 
1. A process for preparing (2S,5R)-N-(2-aminoethoxy)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo [3.2.1] octane-2-carboxamide represented by the following formula (III-059):

OG Complex Work Unit Chemistry
which comprises:
(i) among the compounds represented by the following formulae (IV-a2), (IV-a3) and (IV-a4):

OG Complex Work Unit Chemistry
wherein in the formula (IV-a2), (IV-a3) or (IV-a4), TFA represents trifluoroacetyl, Boc represents tert-butoxycarbonyl, Teoc represents 2-trimethylsilylethoxycarbonyl, and OBn represents benzyloxy, (ia) subjecting to coupling the compound represented by the formula (IV-a2) or (IV-a4) with tert-butyl 2-(aminooxy) ethylcarbamate in the presence of an active ester, an active amide or a dehydration condensing agent, or (ib) subjecting to coupling the compound represented by the formula (IV-a3) with benzyl 2-(aminooxy) ethylcarbamate in the presence of an active ester, an active amide or a dehydration condensing agent, to prepare a compound represented by the following formula (IV-b2-Boc-059), (IV-b3-Cbz-059) or (IV-b4-Boc-059):

OG Complex Work Unit Chemistry
wherein in the formula (IV-b2-Boc-059), (IV-b3-Cbz-059) or (IV-b4-Boc-059), TFA represents trifluoroacetyl, Boc represents tert-butoxycarbonyl, Cbz represents benzyloxycarbonyl, Teoc represents 2-trimethylsilylethoxycarbonyl, and OBn represents benzyloxy,
(iia) deprotecting the trifluoroacetyl group of the compound represented by the formula (IV-b2-Boc-059) by a treatment with a base to prepare a compound represented by the following formula (IV-c-Boc-059):

OG Complex Work Unit Chemistry
wherein in the formula (IV-c-Boc-059) or (IV-c-Cbz-059), Boc represents tert-butoxycarbonyl, Cbz represents benzyloxycarbonyl, and OBn represents a benzyloxy, or (iib) removing the tert-butoxycarbonyl of the compound represented by the formula (IV-b3-Cbz-059) by an acid treatment to prepare a compound represented by the formula (IV-c-Cbz-059), or (iic) removing the 2-trimethylsilylethoxycarbonyl of the compound represented by the formula (IV-b4-Boc-059) by a fluoride to prepare a compound represented by the formula (IV-c-Boc-059);
(iii) then, after silylating the compound (IV-c-Boc-059) or (IV-c-Cbz-059), carrying out an intramolecular urea formation reaction to prepare a compound represented by the following formula (IIa-Boc-059) or (IIa-Cbz-059):

OG Complex Work Unit Chemistry
wherein in the above formula (IIa-Boc-059) or (IIa-Cbz-059), Boc represents tert-butoxycarbonyl, Cbz represents benzyloxycarbonyl, and OBn represents benzyloxy;
(iva) removing the benzyl of the benzyloxy at the 6-position of the compound represented by the formula (IIa-Boc-059) in the presence of a hydrogenolysis catalyst under a hydrogen atmosphere, or (ivb) removing the benzyl of the benzyloxy at the 6-position of the compound represented by the formula (IIa-Cbz-059) in the presence of a hydrogenolysis catalyst under a hydrogen atmosphere, and simultaneously carrying out a tert-butoxycarbonylation in the presence of di-tert-butoxydicarbonate to prepare a compound represented by the following formula (IIb-Boc-059):

OG Complex Work Unit Chemistry
wherein in the formula (IIb-Boc-059), Boc represents tert-butoxycarbonyl,
(v) sulfating the hydroxyl group at the 6-position of the formula (IIb-Boc-059) to prepare a compound represented by the following formula (III-Boc-059):

OG Complex Work Unit Chemistry
wherein in the formula (III-Boc-059), Boc represents tert-butoxycarbonyl, and M represents H, pyridinium, sodium or tetrabutylammonium; and
(vi) deprotecting the tert-butoxycarbonyl group by an acid treatment.