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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
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HRID 465339 반응식
[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]
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반응물 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

생성물 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
수율 55.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-4f28a8d08fae45c0b1fc84c289a6d0b6
출처 데이터셋
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05153187

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