Sodium Bicarbonate → (2S,4S)-4-Mercapto-2-{4-[2-(p-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 362084ノート

反応式

HRID 362084 の反応式
C(=O)([O-])O.[Na+].FC(F)(F)S(O)(=O)=O.FC(F)(F)S(O)(=O)=O.[SH:22][C@@H:23]1[CH2:27][N:26]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=2)=[O:29])[C@H:25]([C:41]([N:43]2[CH2:48][CH2:47][N:46]([CH2:49][CH2:50][O:51][C:52]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=3)=[O:53])[CH2:45][CH2:44]2)=[O:42])[CH2:24]1>>[SH:22][C@@H:23]1[CH2:27][N:26]([C:28]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=2)=[O:29])[C@H:25]([C:41]([N:43]2[CH2:44][CH2:45][N:46]([CH2:49][CH2:50][O:51][C:52]([O:54][CH2:55][C:56]3[CH:57]=[CH:58][C:59]([N+:62]([O-:64])=[O:63])=[CH:60][CH:61]=3)=[O:53])[CH2:47][CH2:48]2)=[O:42])[CH2:24]1

参加物

3

反応物 2

HCID 516892Sodium BicarbonateHCID 86747844(2S,4S)-4-Mercapto-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate)

生成物 1

HCID 15814079(2S,4S)-4-Mercapto-2-{4-[2-(p-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(p-nitrobenzyloxycarbonyl)pyrrolidine収率 88.6%

実験手順

20 ml of a 5% w/v aqueous solution of sodium hydrogencarbonate was added to 862 mg of (2S,4S)-4-mercapto-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate), and the mixture was extracted with 50 ml of ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of ethyl acetate and methanol as the eluent, to afford 514 mg of the title compound, as a powder.

後処理

  1. extractionthe mixture was extracted with 50 ml of ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and methanol as the eluent

出典と根拠

ORDレコード
ord-0c1a5195b6df45c1ac1fd55750300910
出典データセット
uspto-grants-1999_02
特許番号
US05866564

反応ノート

読み込み中…