ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Phosphate → (1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid acetoxymethyl ester

HRID 465339
ノート
印刷プレビュー

反応式

HRID 465339 の反応式
[Na+].[CH3:2][N:3]1[CH2:7][C@H:6]([S:8][C:9]2[C@H:10]([CH3:23])[C@@H:11]3[C@@H:18]([C@H:19]([OH:21])[CH3:20])[C:17](=[O:22])[N:12]3[C:13]=2[C:14]([O-:16])=[O:15])[CH2:5][C:4]1=[S:24].C(=O)([O-])[O-].[K+].[K+].[C:31]([O:34][CH2:35]I)(=[O:33])[CH3:32].P([O-])([O-])([O-])=O>CN(C)C=O>[C:31]([O:34][CH2:35][O:15][C:14]([C:13]1[N:12]2[C:17](=[O:22])[C@H:18]([C@H:19]([OH:21])[CH3:20])[C@H:11]2[C@@H:10]([CH3:23])[C:9]=1[S:8][C@H:6]1[CH2:7][N:3]([CH3:2])[C:4](=[S:24])[CH2:5]1)=[O:16])(=[O:33])[CH3:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1061PhosphateHCID 11430Potassium CarbonateHCID 11820084Iodomethyl acetateHCID 131717556(1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt

生成物 1

HCID 131717555(1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid acetoxymethyl ester
収率 55.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt (400 mg) is suspended in N,N-dimethylformamide (5 ml), and thereto is added potassium carbonate (146 mg). To the mixture is added acetoxymethyl iodide (275 mg) at 5°-7° C., and the mixture is stirred at the same temperature for one hour. The reaction mixture is poured into phosphate buffer (pH 7.0) and extracted with ethyl acetate. The organic layer is washed with water, dried and concentrated to dryness under reduced pressure. The residue is purified by silica gel column chromatography (eluent, chloroform - chloroform:ethanol=98:2), followed by crystallization from tetrahydrofuran and diethyl ether to give (1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid acetoxymethyl ester (250 mg) as colorless needles.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent, chloroform - chloroform:ethanol=98:2)
  6. customfollowed by crystallization from tetrahydrofuran and diethyl ether

出典と根拠

ORDレコード
ord-4f28a8d08fae45c0b1fc84c289a6d0b6
出典データセット
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05153187

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート