N-Boc deprotection and isolation method for water-soluble zwitterionic compounds.
A highly efficient TMSI-mediated deprotection and direct isolation method to obtain zwitterionic compounds from the corresponding N-Boc derivatives has been developed. This method has been demonstrated in the final deprotection/isolation of the β-lactamase inhibitor MK-7655 as a part of its manufacturing process. Further application of this process toward other zwitterionic compounds, such as dipeptides and tripeptides, has been successfully developed. Furthermore, a catalytic version of this transformation has been demonstrated in the presence of BSA or BSTFA.
Process Chemistry, Merck Research Laboratories , P.O. Box 2000, Rahway, New Jersey 07065, United States.
Zhijian
Z
Liu
Nobuyoshi
N
Yasuda
Michael
M
Simeone
Robert A
RA
Reamer
D053961:Azabicyclo Compounds / Q000737:chemistry* / Q000302:isolation & purification*; D004151:Dipeptides / Q000737:chemistry*; D015394:Molecular Structure; D012995:Solubility; D014297:Trimethylsilyl Compounds / Q000737:chemistry*; D014867:Water; D065093:beta-Lactamase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification*
D053961:Azabicyclo Compounds; D004151:Dipeptides; D014297:Trimethylsilyl Compounds; D065093:beta-Lactamase Inhibitors; D014867:Water; C047270:N,N-bis(trimethylsilyl)-2,2,2-trifluoroacetamide; C568736:relebactam