تفاعل #2468028

ord-3d19b2d8cb284c9a825b44ccbd21bf40

معادلة التفاعل

CCOC(=O)[C@@]1(N)[C@H]2[C@@H](C[C@H]1S(=O)(=O)Cc1ccc(Cl)c(Cl)c1)[C@]2(F)C(=O)OCC
(1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester
[Na+].[OH-]
sodium hydroxide
N[C@]1(C(=O)O)[C@H]2[C@@H](C[C@H]1S(=O)(=O)Cc1ccc(Cl)c(Cl)c1)[C@]2(F)C(=O)O
(1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid
المردود 79.6%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةcooled
  2. 2
    أخرىpurified by ion exchange resin (AG 50W-X8 Resin (H form), eluent

الإجراء التجريبي

108 mg of (1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester was stirred in 1.08 mL of 60% sulfuric acid (W/V %) for 3 days at 130° C. The reaction solution was ice-cooled, and neutralized with an aqueous solution of 5N sodium hydroxide. The mixture was stirred for 1 hour at room temperature, and then purified by ion exchange resin (AG 50W-X8 Resin (H form), eluent:water, a 30% aqueous solution of tetrahydrofuran, and a 10% aqueous solution of pyridine), thereby yielding 76 mg of (1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08258133B2uspto-grants-2012_09