HCID 15297072、化合物 → HCID 178491728、化合物

HRID 2289043ノート

反応式

HRID 2289043 の反応式
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][S:8][C@@H:9]2[CH2:13][N:12]([CH3:14])[C@H:11]([C:15]([OH:17])=O)[CH2:10]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.[N+:27]([C:30]1[CH:65]=[CH:64][C:33]([CH2:34][O:35][C:36]([N:38]=[C:39]([NH:50][C:51]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][C:58]([N+:61]([O-:63])=[O:62])=[CH:57][CH:56]=2)=[O:52])[NH:40][CH2:41][C:42]([NH:44][C@H:45]2[CH2:49][CH2:48][NH:47][CH2:46]2)=[O:43])=[O:37])=[CH:32][CH:31]=1)([O-:29])=[O:28]>C(#N)C.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>[N+:27]([C:30]1[CH:65]=[CH:64][C:33]([CH2:34][O:35][C:36]([N:38]=[C:39]([NH:50][C:51]([O:53][CH2:54][C:55]2[CH:56]=[CH:57][C:58]([N+:61]([O-:63])=[O:62])=[CH:59][CH:60]=2)=[O:52])[NH:40][CH2:41][C:42]([NH:44][C@H:45]2[CH2:49][CH2:48][N:47]([C:15]([C@@H:11]3[CH2:10][C@H:9]([S:8][CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=4)[CH2:13][N:12]3[CH3:14])=[O:17])[CH2:46]2)=[O:43])=[O:37])=[CH:32][CH:31]=1)([O-:29])=[O:28]

参加物

6

反応物 2

HCID 15297072HCID 15297072、化合物HCID 178521336HCID 178521336、化合物

生成物 1

HCID 178491728HCID 178491728、化合物収率 95.7%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 81531Diisopropylethylamine溶媒

反応条件

温度
40 °C

実験手順

1.09 g of (2S,4S)-4-(4-methoxybenzylthio)-1-methylpyrrolidine-2-carboxylic acid were suspended in 30 ml of dry acetonitrile, and 691 mg of N,N'-carbonyldiimidazole were added to this suspension, after which the mixture was stirred at 40° C. for 1 hour. At the end of the time, the reaction mixture was cooled with ice, and 2.98 g of (3S)-3-[2-[2,3-bis(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidine trifluoroacetate in 30 ml of dry acetonitrile and 1.7 ml of diisopropylethylamine were added to the mixture, which was then stirred at room temperature overnight. At the end of this time, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The ethyl acetate solution was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The resulting residue was subjected to silica gel column chromatography, eluted with 10% and 20% methanol-ethyl acetate. The fraction containing the desired compound was concentrated by evaporation under reduced pressure to obtain 2.99 g of (2S,4S)-2-[(3S)-3-[2-[2,3-bis(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]-4-(4-methoxybenzylthio)-1-methylpyrrolidine, as a powder.

後処理

  1. additionwere added to the mixture, which
  2. stirringwas then stirred at room temperature overnight
  3. washwashed with water and brine
  4. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. washeluted with 10% and 20% methanol-ethyl acetate
  7. additionThe fraction containing the desired compound
  8. concentrationwas concentrated by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-8d6faadb79ca45019424dd17e1e2c3fe
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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