Phosphate → (2R,3S)-3-Phenoxyacetylamino-2-[(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester

HRID 345631

反応式

HRID 345631 の反応式
C(O)(=O)C(O)=O.[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][CH2:13][CH:14]1[CH2:17][C:16](=[O:18])[N:15]1[CH2:19][C:20]([O:22][CH3:23])=[O:21].[O:24]([CH2:31][C:32]([O:34]C)=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.P([O-])([O-])([O-])=O.[OH-].[K+].CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)[N:46]2[C@H]1C(O)=O>O>[O:24]([CH2:31][C:32]([NH:46][C@@H:17]1[C:16](=[O:18])[N:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C@@H:14]1[CH2:13][CH2:12][C:8]1[O:7][CH:11]=[CH:10][CH:9]=1)=[O:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

7

反応条件

温度
28 °C

実験手順

A 100 mg sample of [(2R,3S),(2S,3R)]-3-amino- <2-[2-(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester oxalate salt and a 135 mg sample of methyl phenoxyacetate were added to 0.lM phosphate buffer (100 ml final volume) and adjusted to pH=6.0 with lN KOH. Milli-Q™ H2O washed Sclavo penicillin G amidase (40 I.U. of enzyme per gram of substrate) was then added to the reaction mixture and the pH of reaction mixture was maintained at 6.0 and temperature at 28° C. for 8 hours. The reaction mixture was then filtered to remove the immobilized enzyme and extracted two times with ethyl acetate. The organic extracts were then dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The title compound was then isolated by column chromatography from this residue using a Kiesegel 60™ column eluted with toluene/ethyl acetate (70/30). Yield: 13%.

後処理

  1. customthe pH of reaction mixture
  2. filtrationThe reaction mixture was then filtered
  3. customto remove the immobilized enzyme
  4. extractionextracted two times with ethyl acetate
  5. dry with materialThe organic extracts were then dried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness in vacuo

出典と根拠

ORDレコード
ord-678c2905b4724c37ac1f44b76fa1f741
出典データセット
uspto-grants-1991_10
特許番号
US05057607

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