Diethyl Ether → HCID 178480560、化合物

HRID 2289044ノート

反応式

HRID 2289044 の反応式
[N+:1]([C:4]1[CH:57]=[CH:56][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:42][C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])[NH:14][CH2:15][C:16]([NH:18][C@H:19]2[CH2:23][CH2:22][N:21]([C:24]([C@@H:26]3[CH2:30][C@H:29]([S:31]CC4C=CC(OC)=CC=4)[CH2:28][N:27]3[CH3:41])=[O:25])[CH2:20]2)=[O:17])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].FC(F)(F)S(O)(=O)=O.CCOCC>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[N+:1]([C:4]1[CH:57]=[CH:56][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:42][C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])[NH:14][CH2:15][C:16]([NH:18][C@H:19]2[CH2:23][CH2:22][N:21]([C:24]([C@@H:26]3[CH2:30][C@H:29]([SH:31])[CH2:28][N:27]3[CH3:41])=[O:25])[CH2:20]2)=[O:17])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 62406Trifluoromethanesulfonic acidHCID 178491728HCID 178491728、化合物

生成物 1

HCID 178480560HCID 178480560、化合物収率 63.7%

試薬・触媒・溶媒 2

HCID 6422Trifluoroacetic acid溶媒HCID 7519Anisole溶媒

実験手順

2.99 g of (2S,4S)-2-[(3S)-3-[2-[2,3-bis(4-nitrobenzyloxycarbonyl)guanidino]acetylanino]pyrrolidin-1-ylcarbonyl]-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (1) above] were dissolved in a mixture of 21 ml of trifluoroacetic acid and 4.1 ml of anisole, and then 1.15 ml of trifluoromethanesulfonic acid were added dropwise, whilst stirring and ice-cooling, to the resulting solution. The reaction mixture was stirred for 20 minutes at room temperature, after which the mixture was poured into ether. The resulting precipitate was collected by filtration and the precipitate was dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated sodium hydrogencarbonate, with water and with brine and dried over anhydrous sodium sulfate. The ethyl acetate solution was concentrated by evaporation under reduced pressure to obtain 1.62 g of (2S,4S)-2-[(3S)-3-[2-[2,3-bis(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]-4-mercapto-1-methylpyrrolidine, in the form of an amorphous powder.

後処理

  1. temperatureice-cooling, to the resulting solution
  2. stirringThe reaction mixture was stirred for 20 minutes at room temperature
  3. filtrationThe resulting precipitate was collected by filtration
  4. dissolutionthe precipitate was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with saturated sodium hydrogencarbonate, with water and with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe ethyl acetate solution was concentrated by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-7fa6fb63f91544beac568ecf3fbee1fa
出典データセット
uspto-grants-2000_07
特許番号
US06090802

反応ノート

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