Sodium Sulfite → HCID 57036270、化合物

HRID 1490363ノート

反応式

HRID 1490363 の反応式
[CH2:1]([N:3]([CH2:38][CH3:39])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12][C:13]1[C@H:14]([CH3:37])[C@@H:15]2[C@@H:32]([C@H:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]2[C:17]=1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:19])=[O:5])[CH3:2].C(=O)([O-])[OH:41].[Na+].ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:38]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([C:13]1[C@H:14]([CH3:37])[C@@H:15]2[C@@H:32]([C@H:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]2[C:17]=1[C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=1)=[O:19])=[O:41])=[O:5])[CH3:39]

参加物

6

反応物 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 570929914-Nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

生成物 1

HCID 57036270HCID 57036270、化合物収率 25%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

10 ml of a methylene cloride solution containing 554 mg (1.00 mmol) of 4-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 37) were cooled in an ice bath, and then 1.5 ml (1.5 mmol) of a 1M aqueous solution of sodium hydrogencarbonate and then 215 mg (1.00 mmol) of m-chloroperbenzoic acid (80% purity) were added, and the reaction solution was stirred for 90 minutes at the same temperature. At the end of this time, an aqueous solution of sodium sulfite was added to the reaction solution, and the mixture was stirred for 10 minutes to complete the reaction. The reaction solution was then diluted with methylene chloride, ice-cooled, washed with an aqueous solution of sodium hydrogencarbonate and condensed by evaporation under reduced pressure. The resulting residue was purified by column chromatography through 50 g of silica gel. Elution with ethyl acetate afforded 145 mg (yield 25%) of an isomer of the title compound of lower polarity (the isomer is a result of the configuration of the S-oxide), followed by 96 mg (yield 17%) of a higher polarity isomer of the title compound, both as foam-like solids.

後処理

  1. temperaturewere cooled in an ice bath
  2. stirringthe mixture was stirred for 10 minutes
  3. customthe reaction
  4. temperaturecooled
  5. washwashed with an aqueous solution of sodium hydrogencarbonate and condensed by evaporation under reduced pressure
  6. customThe resulting residue was purified by column chromatography through 50 g of silica gel
  7. washElution with ethyl acetate

出典と根拠

ORDレコード
ord-bf45fa73b1b0442da0be04929f0ed662
出典データセット
uspto-grants-1997_10
特許番号
US05681951

反応ノート

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