Title:
METHOD FOR REMOVING TERT-BUTOXYCARBONYL GROUPS
Document Type and Number:
WIPO Patent Application WO/2023/132353
Kind Code:
A1
Abstract:
The present invention provides a method for removing tert-butoxycarbonyl (Boc) groups in a compound having Boc groups on nitrogen atoms, wherein the method includes treating the compound in the presence of a trifluoromethanesulfonic acid metal salt (metal triflate: M(OTf)n) or a rare earth metal halide (MXn) and a base and obtaining a compound in which the Boc groups are converted into H-.
Inventors:
ITO TAISUKE (JP)
KAMAKURA DAIKI (JP)
HAYASE TADAKATSU (JP)
KAMAKURA DAIKI (JP)
HAYASE TADAKATSU (JP)
Application Number:
PCT/JP2023/000123
Publication Date:
July 13, 2023
Filing Date:
January 06, 2023
Export Citation:
Assignee:
CHUGAI PHARMACEUTICAL CO LTD (JP)
International Classes:
C07B51/00; C07C209/62; C07C211/29; C07C211/45; C07C211/58; C07D211/26; C07D213/16; C07D295/03; C07D401/10; C40B50/14
Other References:
ZACHARY Z. GULLEDGE; JESSE D. CARRICK: "Deprotection of N‐tert‐Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition–Elimination with 3‐Methoxypropylamine", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2020, no. 12, 13 March 2020 (2020-03-13), DE , pages 1817 - 1822, XP072120293, ISSN: 1434-193X, DOI: 10.1002/ejoc.201901811
SUBHAS BOSE D., KIRAN KUMAR K., NARSIMHA REDDY A. V.: "-Boc) with Sn(OTf) 2", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 33, no. 3, 3 January 2003 (2003-01-03), US , pages 445 - 450, XP093078197, ISSN: 0039-7911, DOI: 10.1081/SCC-120015775
JIH, R.H. MOTI, L.J. SHWU-CHEN, T. HAKIMELAHI, G.H.: "Ceric Ammonium Nitrate in the Deprotection of tert-Butoxycarbonyl Group", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 37, no. 12, 18 March 1996 (1996-03-18), Amsterdam , NL , pages 2035 - 2038, XP004029853, ISSN: 0040-4039, DOI: 10.1016/0040-4039(96)00211-0
NIGAMA SATISH C., MANN ANDRÉ, TADDEI MAURIZIO, WERMUTHA CAMILLE-GEORGESL. : "Selective Removal of the Tert-Butoxycarbonyl Group from Secondary Amines: ZnBr2 as the Deprotecting Reagent", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 19, no. 18, 1 January 1989 (1989-01-01), US , pages 3139 - 3142, XP009547431, ISSN: 0039-7911, DOI: 10.1080/00397918908052712
EVANS EMILY F., LEWIS NORMAN J., KAPFER ISABELLE, MACDONALD GREGOR, TAYLOR RICHARD J. K.: "N-tert -Butoxycarbonyl (BOC) Deprotection Using Boron Trifluoride Etherate", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 27, no. 11, 1 June 1997 (1997-06-01), US , pages 1819 - 1825, XP093078202, ISSN: 0039-7911, DOI: 10.1080/00397919708006783
SUBHAS BOSE D., KIRAN KUMAR K., NARSIMHA REDDY A. V.: "-Boc) with Sn(OTf) 2", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 33, no. 3, 3 January 2003 (2003-01-03), US , pages 445 - 450, XP093078197, ISSN: 0039-7911, DOI: 10.1081/SCC-120015775
JIH, R.H. MOTI, L.J. SHWU-CHEN, T. HAKIMELAHI, G.H.: "Ceric Ammonium Nitrate in the Deprotection of tert-Butoxycarbonyl Group", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 37, no. 12, 18 March 1996 (1996-03-18), Amsterdam , NL , pages 2035 - 2038, XP004029853, ISSN: 0040-4039, DOI: 10.1016/0040-4039(96)00211-0
NIGAMA SATISH C., MANN ANDRÉ, TADDEI MAURIZIO, WERMUTHA CAMILLE-GEORGESL. : "Selective Removal of the Tert-Butoxycarbonyl Group from Secondary Amines: ZnBr2 as the Deprotecting Reagent", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 19, no. 18, 1 January 1989 (1989-01-01), US , pages 3139 - 3142, XP009547431, ISSN: 0039-7911, DOI: 10.1080/00397918908052712
EVANS EMILY F., LEWIS NORMAN J., KAPFER ISABELLE, MACDONALD GREGOR, TAYLOR RICHARD J. K.: "N-tert -Butoxycarbonyl (BOC) Deprotection Using Boron Trifluoride Etherate", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 27, no. 11, 1 June 1997 (1997-06-01), US , pages 1819 - 1825, XP093078202, ISSN: 0039-7911, DOI: 10.1080/00397919708006783
Attorney, Agent or Firm:
YAMAMOTO, Osamu et al. (JP)
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