Lactic Acid → cis-4-Oxo-3-phenoxyacetylamino-2-p-toluenesulfonyloxymethylazetidine

HRID 2050383ノート

反応式

HRID 2050383 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][C@H:14]1[C@@H:17]([NH:18][C:19](=[O:28])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16](=[O:29])[NH:15]1.C(O)(=O)C(C)O.CCCCCC>N1C=CC=CC=1.C(OCC)(=O)C>[O:29]=[C:16]1[NH:15][C@@H:14]([CH2:13][O:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[C@H:17]1[NH:18][C:19](=[O:28])[CH2:20][O:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

7

反応物 4

HCID 612Lactic AcidHCID 73974-Toluenesulfonyl chlorideHCID 8058HexaneHCID 70579374HCID 70579374、化合物

生成物 1

HCID 86734329cis-4-Oxo-3-phenoxyacetylamino-2-p-toluenesulfonyloxymethylazetidine

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of 4.30 g (0.022 mole) of 98% p-toluenesulfonyl chloride in 24 ml of anhydrous pyridine at 0° (ice bath) was added 2.64 g (0.011 mole) of cis-2-hydroxymethyl-4-oxo-3-phenoxyacetylaminoazetidine in one portion. The solution was stirred at 0° for 3 hours then was stored at -25° overnight. After warming to 0°, 1.0 ml of 85% lactic acid was added and stirring was continued for 1 hour. The reaction mixture was poured into ethyl acetate and extracted successively with water, dilute aqueous hydrochloric acid, aqueous sodium bicarbonate and brine and was dried (MgSO4). Filtration followed by removal of the solvent in vacuo resulted in a yellow solid. Clarification of a hot solution of this material in ethyl acetate (375 ml), followed by the addition of hexane (200 ml) and recrystallization afforded cis-4-oxo-3-phenoxyacetylamino-2-p-toluenesulfonyloxymethylazetidine; tlc: ethyl acetate, silica gel GF, Rf=0.47; mp 136° (dec.).

後処理

  1. waitthen was stored at -25° overnight
  2. temperatureAfter warming to 0°
  3. stirringstirring
  4. waitwas continued for 1 hour
  5. extractionextracted successively with water, dilute aqueous hydrochloric acid, aqueous sodium bicarbonate and brine
  6. dry with materialwas dried (MgSO4)
  7. filtrationFiltration
  8. customfollowed by removal of the solvent in vacuo
  9. customresulted in a yellow solid

出典と根拠

ORDレコード
ord-610353e665a1442190ff2f8ae998d3f0
出典データセット
uspto-grants-1980_04
特許番号
US04200572

反応ノート

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