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Process for synthesizing ergothioneine and related compounds
专利权人:
发明人:
Moegamat Anwar Jardine,Lutete Peguy Khonde
申请号:
US15513237
公开号:
US09908854B2
申请日:
2015.09.22
申请国别(地区):
US
年份:
2018
代理人:
摘要:
The invention provides a process for synthesising a compound of formula Vwherein:n is 0, 1 or 2 andR is H oror a physiologically acceptable salt, tautomer, stereoisomer or mixture of stereoisomers thereof. The process utilizes a N-benzyl protected histidine rather than the unprotected form of histidine. The process of the invention comprises the steps of: (a) deprotecting a N-benzyl protected histidine of formula 11 to form N-benzyl histidine of formula 12 (b) converting compound 12 to (S)-3-(1-benzyl-1H-imidazol-4-yl)-2-(dimethylamino)propanoic acid of formula 13 (c) converting compound 13 to (2S)-N,N,N-2-trimethylethanaminium-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid of formula 14 (d) brominating the imidazole ring of the compound of formula 14 to form 5-bromohercynine lactone (reactive intermediate) and (e) converting the 5-bromohercynine lactone of step (d) to (β-amino-β-carboxyethyl)ergothioneine sulfide of formula 15. The process optionally further includes one of steps (f) to (h): (f) converting the compound of formula 15 to a sulfoxide (g) converting the compound of formula 15 to a sulfone or (h) converting the compound of formula 15 to ergothioneine (ESH).
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