Trifluoroacetic acid → Hexahydropyrazino[2,1-c][1,4]thiazin-9(6H)-one 2,2-dioxide

HRID 2074834ノート

反応式

HRID 2074834 の反応式
CC(OC([NH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][S:14](=[O:18])(=[O:17])[CH2:13][CH:12]1[C:19]([O:21]C)=O)=O)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:13]1[CH:12]2[C:19](=[O:21])[NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][S:14]1(=[O:17])=[O:18]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 59215870Methyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-3-thiomorpholinecarboxylate 1,1-dioxide

生成物 1

HCID 59215885Hexahydropyrazino[2,1-c][1,4]thiazin-9(6H)-one 2,2-dioxide収率 91.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of methyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-3-thiomorpholinecarboxylate 1,1-dioxide (D17; 295 mg, 0.88 mmol) in 3 ml of anhydrous dichloromethane was added 1 ml of trifluoroacetic acid and the resulting solution was stirred at room temperature under nitrogen for 1 h 30 min. The solvent was removed under reduced pressure and the residue loaded on a SCX column, washed with methanol and eluted with methanolic ammonia. The product was purified further by chromatography (silica cartridge, cyclohexane to ethyl acetate, then dichloromethane to dichloromethane:methanol 70:30) to give 165 mg of the target compound.

後処理

  1. customThe solvent was removed under reduced pressure
  2. washwashed with methanol
  3. washeluted with methanolic ammonia
  4. customThe product was purified further by chromatography (silica cartridge, cyclohexane to ethyl acetate

出典と根拠

ORDレコード
ord-8095dd1fd7d84b20859cacf945e552cb
出典データセット
uspto-grants-2011_04
特許番号
US07919491B2

反応ノート

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