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

HRID 1974179Notes

Reaction equation

HRID 1974179 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-462c6eb0ec334873a2b34c88d6f0369c
Source dataset
uspto-grants-1976_12
Patent number
US04000154

Reaction notes

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