Triethylamine → HCID 56634706, compound

HRID 1905098Notes

Reaction equation

HRID 1905098 reaction equation
C(N(CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(O[CH:24]1[NH:27][C:26](=[O:28])[CH2:25]1)(=O)C.[Cl:29][CH2:30][C:31](=[O:42])[C:32](=[N+:40]=[N-:41])[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>ClCCl>[C:36]([O:35][C:33]([C:32](=[N+:40]=[N-:41])[C:31](=[O:42])[CH:30]([CH:24]1[NH:27][C:26](=[O:28])[CH2:25]1)[Cl:29])=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 1199814-Acetoxy-2-azetidinoneHCID 56611923HCID 56611923, compound

Product 1

HCID 56634706HCID 56634706, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.8 ml (13.0 mmol - 2.6 equivalents) of triethylamine and then 2.3 ml (12.0 mmol - 2.4 equivalents) of trimethylsilyl trifluoromethanesulphonate were added to a solution, which had been cooled to 0° C., of 646 mg (5.0 mmol) of 4-acetoxy-2-azetidinone and 1.42 g (6.5 mmol) of tert.-butyl 4-chloro-2-diazo-3-oxobutanoate in 45 ml of anhydrous dichloromethane. The cooling bath was removed and the mixture was stirred at room temperature for 5 h, then 0.3 ml (1.5 mmol - 0.3 equivalent) of trimethylsilyl trifluoromethanesulphonate was added and the mixture was stirred at room temperature for 1 h. To work up, it was poured into a mixture of cold saturated NaHCO3 solution and ethyl acetate, extraction with ethyl acetate was carried out, and the organic extracts were washed with saturated NaCl solution and dried over MgSO4. After evaporation of the solvent in vacuo and chromatography on 40 g of silica gel (toluene:ethyl acetate 1:1), 426 mg (30%) of the title compound were obtained as a mixture of diastereomers (10:1), Rf: 0.35 (toluene:ethyl acetate 1:1).

Workup

  1. customThe cooling bath was removed
  2. addition0.3 ml (1.5 mmol - 0.3 equivalent) of trimethylsilyl trifluoromethanesulphonate was added
  3. stirringthe mixture was stirred at room temperature for 1 h
  4. additionit was poured into a mixture of cold saturated NaHCO3 solution and ethyl acetate, extraction with ethyl acetate
  5. washthe organic extracts were washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customAfter evaporation of the solvent in vacuo and chromatography on 40 g of silica gel (toluene:ethyl acetate 1:1)

Sources & evidence

ORD record
ord-129091a8d0d741d6a344fc0c321ee91b
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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