1-Hydroxybenzotriazole → HCID 56998234, 화합물

HRID 2289083노트

반응식

HRID 2289083 반응식
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]

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57256052HCID 57256052, 화합물HCID 70273891HCID 70273891, 화합물

생성물 1

HCID 56998234HCID 56998234, 화합물수율 68.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-d9832ee8544743d39c2c101ea7d78af2
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06090802

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