Triethylamine → HCID 137329129, compound

HRID 1905097Notes

Reaction equation

HRID 1905097 reaction equation
C(N(CC)CC)C.C(O[C@H:12]1[NH:15][C:14](=[O:16])[C@@H:13]1[C@H:17]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:18][O:19][SiH:20]([CH3:22])[CH3:21])(=O)C.[N+:27](=[C:29]([C:36](=[O:38])[CH3:37])[C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])=[N-:28].FC(F)(F)S(O[Si](C)(C)C)(=O)=O>ClCCl>[C:23]([C@@H:17]([C@H:13]1[C@@H:12]([CH2:37][C:36](=[O:38])[C:29]([C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])=[N+:27]=[N-:28])[NH:15][C:14]1=[O:16])[CH2:18][O:19][SiH:20]([CH3:21])[CH3:22])([CH3:24])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 541706512-Diazonio-3-oxo-1-[(prop-2-en-1-yl)oxy]but-1-en-1-olateHCID 131715976HCID 131715976, compound

Product 1

HCID 137329129HCID 137329129, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.2 ml (52 mmol - 2.6 equivalents) of triethylamine are added to a solution, which has been cooled to 0° C., of 5.75 g (20 mmol) of (3R,4R)-4-acetoxy-3-[(1R)-1-tert.-butyldimethylsilyloxyethyl]azetidin-2-one [S. Oida et al. Chem. Pharm. Bull. 29 2899 (1981); M. Shiozaki et al. Tetrahedron 39 2399 (1983)] and 4.37 g (26 mmol - 1.3 equivalents) of allyl 2-diazo-3-oxobutanoate in 190 ml of anhydrous dichloromethane, and then 9.3 ml (48 mmol - 2.4 equivalents) of trimethylsilyl trifluoromethanesulphonate are added dropwise. The cooling bath was removed, and the mixture was stirred at room temperature for 1 h, 1.55 ml (8 mmol - 0.4 equivalent) of trimethylsilyl trifluoromethanesulphonate were added, and the mixture was stirred for a further 0.5 h at room temperature. The reaction solution was then poured into a mixture of cold, saturated NaHCO 3 solution and ethyl acetate, and extraction with ethyl acetate was carried out, and the combined organic extracts were washed with saturated NaCl solution and dried over MgSO4. The solvent was evaporated in vacuo, and the residue was filtered through 150 g of silica gel (toluene:ethyl acetate 4:1). 6.4 g (81%) of the title compound were obtained as pale crystals, melting point: 66° C., Rf: 0.33 (toluene:ethyl acetate 7:3) [α]D20 =59.2° (c 0.969, CHCl3).

Workup

  1. customThe cooling bath was removed
  2. addition1.55 ml (8 mmol - 0.4 equivalent) of trimethylsilyl trifluoromethanesulphonate were added
  3. stirringthe mixture was stirred for a further 0.5 h at room temperature
  4. additionThe reaction solution was then poured into a mixture of cold,
  5. extractionsaturated NaHCO 3 solution and ethyl acetate, and extraction with ethyl acetate
  6. washthe combined organic extracts were washed with saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated in vacuo
  9. filtrationthe residue was filtered through 150 g of silica gel (toluene:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-f9b997cfeec642e69cd8327858ad2e98
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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