Dimethylformamide → (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid isobutyryloxymethyl ester

HRID 465337노트

반응식

HRID 465337 반응식
[K+].[NH:2]1[CH2:6][C@H:5]([S:7][C:8]2[C@H:9]([CH3:22])[C@@H:10]3[C@@H:17]([C@H:18]([OH:20])[CH3:19])[C:16](=[O:21])[N:11]3[C:12]=2[C:13]([O-:15])=[O:14])[CH2:4][C:3]1=[S:23].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[C:35]([O:40][CH2:41]I)(=[O:39])[CH:36]([CH3:38])[CH3:37]>C(OCC)(=O)C>[C:35]([O:40][CH2:41][O:14][C:13]([C:12]1[N:11]2[C:16](=[O:21])[C@H:17]([C@H:18]([OH:20])[CH3:19])[C@H:10]2[C@@H:9]([CH3:22])[C:8]=1[S:7][C@H:5]1[CH2:6][NH:2][C:3](=[S:23])[CH2:4]1)=[O:15])(=[O:39])[CH:36]([CH3:38])[CH3:37]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10376456Iodomethyl 2-methylpropanoateHCID 131717553(1R, 5S, 6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid potassium salt

생성물 1

HCID 9955020(1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid isobutyryloxymethyl ester수율 30.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of (1R, 5S, 6S)-2-[(4R)-pyrrolidine-2- thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2- em-3-carboxylic acid potassium salt (0.34 g), N,N-dimethylformamide (3 ml) and potassium carbonate (0.12 g) is added dropwise isobutyryloxymethyl iodide (0.27 g) under ice cooling. After stirring the mixture at the same temperature for 30 minutes, ethyl acetate (10 ml) is added to the reaction mixture, and the mixture is washed with water, and the organic layer is dried and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel flash column chromatography (eluent, chloroform: ethanol=20:1), followed by crystallization from isopropyl ether and ethyl acetate to give (1R, 5S, 6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid isobutyryloxymethyl ester (0.12 g) as colorless needles.

후처리

  1. washthe mixture is washed with water
  2. customthe organic layer is dried
  3. customevaporated under reduced pressure
  4. customto remove the solvent
  5. customThe residue is purified by silica gel flash column chromatography (eluent, chloroform: ethanol=20:1)
  6. customfollowed by crystallization from isopropyl ether and ethyl acetate

출처 및 근거

ORD 기록
ord-0077f6b3fd504099ae3ffac10bcbd483
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153187

반응 노트

불러오는 중…