1-Hydroxybenzotriazole → HCID 56998234、化合物

HRID 2289083ノート

反応式

HRID 2289083 の反応式
FC(F)(F)C(O)=O.[CH3:8][N:9]([C@H:23]1[CH2:27][CH2:26][NH:25][CH2:24]1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11].C(N(CC)C(C)C)(C)C.[C:37]([CH2:40][CH:41]([C@@H:43]1[CH2:47][C@H:46]([S:48][CH2:49][C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)[CH2:45][N:44]1[C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][C:65]([N+:68]([O-:70])=[O:69])=[CH:64][CH:63]=1)=[O:59])[OH:42])(O)=[O:38].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[OH:42][CH:41]([C@@H:43]1[CH2:47][C@H:46]([S:48][CH2:49][C:50]2[CH:51]=[CH:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=2)[CH2:45][N:44]1[C:58]([O:60][CH2:61][C:62]1[CH:63]=[CH:64][C:65]([N+:68]([O-:70])=[O:69])=[CH:66][CH:67]=1)=[O:59])[CH2:40][C:37]([N:25]1[CH2:26][CH2:27][C@H:23]([N:9]([CH3:8])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:24]1)=[O:38]

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57256052HCID 57256052、化合物HCID 70273891HCID 70273891、化合物

生成物 1

HCID 56998234HCID 56998234、化合物収率 68.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

In dimethylformamide (5 ml), (3S)-3-[N-methyl-N-(4-nitrobenzyloxycarbonyl)amino]pyrrolidine trifluoroacetate (400.9 mg) was dissolved. To the solution, N,N-diisopropylethylamine (0.444 ml) and a solution of (2S,4S)-2-(2-carboxy-1-hydroxyethyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.5 g) in dimethylformamide (5 ml), were added at room temperature. To the resulting mixture, 1-hydroxybenzotriazole (151.5 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (273.5 mg) and water (1 ml) were added successively and the mixture was stirred overnight at the same temperature. The reaction mixture was concentrated by evaporation under reduced pressure. Ethyl acetate was then added to the residue. The resulting mixture was washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column (ethyl acetate methanol=50:1), whereby (2S,4S)-2-[1-hydroxy-2-[(3S)-3-[N-methyl-N-(4-nitrobenzyloxycarbonyl)amino]pyrrolidin-1-ylcarbonyl]ethyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (523.5 mg) was obtained

後処理

  1. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  2. additionEthyl acetate was then added to the residue
  3. washThe resulting mixture was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by chromatography through a silica gel column (ethyl acetate methanol=50:1)

出典と根拠

ORDレコード
ord-d9832ee8544743d39c2c101ea7d78af2
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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