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

HRID 1974179노트

반응식

HRID 1974179 반응식
[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

참가 물질

7

반응물 4

HCID 612Lactic AcidHCID 73974-Toluenesulfonyl chlorideHCID 8058HexaneHCID 70579374HCID 70579374, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매2회

실험 절차

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-toluenesulfonyloxymethyl-azetidine; tlc: ethyl acetate, silica gel GF, Rf = 0.47; mp 136°(dec.).

후처리

  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

출처 및 근거

ORD 기록
ord-462c6eb0ec334873a2b34c88d6f0369c
출처 데이터셋
uspto-grants-1976_12
특허 번호
US04000154

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