Tetrahydrofuran → HCID 86740767, compound

HRID 279786Notes

Reaction equation

HRID 279786 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@@H:8]([CH2:11][CH3:12])[C@@H:7]1[C:13]([OH:15])=O.O1CCCC1.C(N(CC)CC)C.[N+:34](=[CH2:36])=[N-:35]>CCOCC>[N+:34](=[CH:36][C:13]([C@@H:7]1[N:6]([CH2:5][C:4]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:3]=2[O:2][CH3:1])[C:9](=[O:10])[C@H:8]1[CH2:11][CH3:12])=[O:15])=[N-:35]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9550DiazomethaneHCID 14211461HCID 14211461, compound

Product 1

HCID 86740767HCID 86740767, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of 14.65 g (50 millimoles) of trans-1-(2,4-dimethoxy-benzyl)-3-ethyl-4-oxo-2-azetidinecarboxylic acid prepared according to the preceding paragraph in 150 ml of anhydrous tetrahydrofurane 7.3 ml (52.5 millimoles) of triethyl amine are added and to the solution under stirring and ice-cooling 5.1 ml (52.5 millimoles) of ethyl-chloro-formiate are added. The mixture is cooled to -15° C., stirred at this temperature for 20 minutes and the precipitated triethyl amine salt is filtered off under argon. To the filtrate a cold solution of 22.5 g (150 millimoles) of diazomethane and 230 ml of ether is added. The solution is allowed to warm to room temperature under stirring and after 2 hours the reaction mixture is evaporated to dryness. The residue is a mixture comprising predominantly trans-4-diazoacetyl-1-(2,4-dimethoxy-benzyl)-3-ethyl-2-azetidinone and some methyl-trans-1-(2,4-dimethoxybenzyl)-3-ethyl-4-oxo-2-azetidine-carboxylate. The mixture thus obtained can be used as starting material in Example 3 directly, without purification. The benzene solution of the evaporation residue can be, however, subjected to column chromatography, if desired. (Adsorbent: Kieselgel 60. diameter 0.063-0.200 mm, eluant: benzene-acetone 7:2). Thus 9.2 g of trans-4-diazoacetyl-1-(2,4-dimethoxy-benzyl)-3-ethyl-2-azetidinone are obtained. Yield: 59%.

Workup

  1. additionare added and to the solution
  2. temperatureice-cooling 5.1 ml (52.5 millimoles) of ethyl-chloro-formiate
  3. additionare added
  4. stirringstirred at this temperature for 20 minutes
  5. filtrationthe precipitated triethyl amine salt is filtered off under argon
  6. temperatureto warm to room temperature
  7. stirringunder stirring and after 2 hours the reaction mixture
  8. customis evaporated to dryness
  9. customThe mixture thus obtained can
  10. customwithout purification

Sources & evidence

ORD record
ord-fcafa4ef84cf4ae1a6ada5b2bef4f8ea
Source dataset
uspto-grants-1986_05
Patent number
US04587049

Reaction notes

Loading…