Thioglycolic Acid → (2S,5R)-1-tert-butyl 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate

HRID 515588ノート

反応式

HRID 515588 の反応式
O[Li].O.SCC(O)=O.[CH2:9]([O:16][N:17]([C@H:30]1[CH2:35][N:34]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@H:33]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:32][CH2:31]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C.O>[CH2:9]([O:16][NH:17][C@H:30]1[CH2:35][N:34]([C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])[C@H:33]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:32][CH2:31]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86700664(2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate

生成物 1

HCID 86700665(2S,5R)-1-tert-butyl 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate収率 85%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

LiOH.H2O (95 g, 2.3 mol) and 2-mercaptoacetic acid (124 g, 1.3 mol) were added to a solution of (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate (251 g, 0.45 mol) in DMF (1200 mL). The reaction mixture was then stirred at 20° C. overnight. The reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic layer was washed with brine (3×), concentrated in vacuum and purified by silica gel column chromatography (3; 1 petroleum ether/EtOAc) to afford (2S,5R)-1-tert-butyl 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate (122.9 g, 85%) as a yellow solid.

後処理

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layer was washed with brine (3×)
  3. concentrationconcentrated in vacuum
  4. custompurified by silica gel column chromatography (3; 1 petroleum ether/EtOAc)

出典と根拠

ORDレコード
ord-48f289f89ad14ebcb6117d2be84d5c1d
出典データセット
uspto-grants-2015_08
特許番号
US09108966B2

反応ノート

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