Ethyl Acetate → HCID 131721431、化合物

HRID 1601013ノート

反応式

HRID 1601013 の反応式
[OH:1][C@@H:2]([C@H:4]1[C:39](=[O:40])[N:6]2[C:7]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])=[C:8](OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[SH:41][C@@H:42]1[CH2:46][N:45]([CH3:47])[C@H:44]([C:48]([N:50]2[CH2:54][CH2:53][C@@H:52]([CH2:55][NH:56][C:57]([O:59][CH2:60][C:61]3[CH:66]=[CH:65][C:64]([N+:67]([O-:69])=[O:68])=[CH:63][CH:62]=3)=[O:58])[CH2:51]2)=[O:49])[CH2:43]1.C(OCC)(=O)C>C(#N)C.C(N(CC)C(C)C)(C)C>[OH:1][C@@H:2]([C@H:4]1[C:39](=[O:40])[N:6]2[C:7]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])=[C:8]([S:41][C@@H:42]3[CH2:46][N:45]([CH3:47])[C@H:44]([C:48]([N:50]4[CH2:54][CH2:53][C@@H:52]([CH2:55][NH:56][C:57]([O:59][CH2:60][C:61]5[CH:66]=[CH:65][C:64]([N+:67]([O-:69])=[O:68])=[CH:63][CH:62]=5)=[O:58])[CH2:51]4)=[O:49])[CH2:43]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 15871605p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylateHCID 57208904Carbamic acid, [[(3S)-1-[[(2S,4S)-4-mercapto-1-methyl-2-pyrrolidinyl]carbonyl]-3-pyrrolidinyl]methyl]-, (4-nitrophenyl)methyl ester

生成物 1

HCID 131721431HCID 131721431、化合物収率 78.4%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 81531Diisopropylethylamine溶媒

実験手順

To a solution of 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-(diphenylphosphoryloxy)-1-carbapen-2-em-3-carboxylate (0.73 g) in anhydrous acetonitrile (7 ml), N,N-diisopropylethylamine (0.22 ml) and a solution of (2S,4S)-4-mercapto-1-methyl-2-[(3S)-3-(4-nitrobenzyloxycarbonylaminomethyl)pyrrolidin-1-ylcarbonyl]pyrrolidine (0.57 g) in anhydrous acetonitrile (10 ml) were added while stirring in an ice bath. The resulting mixture was stirred overnight at 0° C. To the reaction mixture, ethyl acetate was added. The resulting mixture was washed with water and saturated saline solution, dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column (ethyl acetate/methanol=7/3), whereby 4-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[(3S)-3-(4-nitrobenzyloxycarbonylaminomethyl)pyrrolidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate (0.78 g) was obtained.

後処理

  1. stirringThe resulting mixture was stirred overnight at 0° C
  2. washThe resulting mixture was washed with water and saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue was purified by chromatography through a silica gel column (ethyl acetate/methanol=7/3)

出典と根拠

ORDレコード
ord-4dc55ea25a284348b77ff4545839a1df
出典データセット
uspto-grants-1999_11
特許番号
US05977097

反応ノート

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