Vinyl Acetate → p-Nitrobenzyl 2-(2-acetoxyaziridin-1-yl)-carbapen-2-em-3-carboxylate

HRID 329674Notes

Reaction equation

HRID 329674 reaction equation
[N:1]([C:4]1[CH2:5][C@@H:6]2[CH2:23][C:22](=[O:24])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10])=[N+]=[N-].[C:25]([O:28][CH:29]=[CH2:30])(=[O:27])[CH3:26].C(=O)(O)[O-].[Na+]>ClCCl>[C:25]([O:28][CH:29]1[CH2:30][N:1]1[C:4]1[CH2:5][C@@H:6]2[CH2:23][C:22](=[O:24])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 7904Vinyl AcetateHCID 516892Sodium BicarbonateHCID 131715741p-Nitrobenzyl 2-azidocarbapen-2-em-3-carboxylate

Product 1

HCID 131715757p-Nitrobenzyl 2-(2-acetoxyaziridin-1-yl)-carbapen-2-em-3-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of p-nitrobenzyl 2-azido-carbapen-2-em-3-carboxylate (11.3 mg, 34 micromol), vinyl acetate (0.1 ml), and solid sodium bicarbonate in dry dichloromethane was kept 2 days at ambient temperature, filtered through florisil, and evaporated under vacuum. The residue was chromatographed on one 15 cm×20 cm 250 micron silica gel preparative thin layer chromatography plate developed with 5:1 (v/v) diethyl ether-ethyl acetate. The band centered at Rf 0.20 was eluted with ethyl acetate and the eluate was evaporated under vacuum to provide 5.5 mg (41%) p-nitrobenzyl 2-(2-acetoxyaziridin-1-yl)-carbapen-2-em-3-carboxylate; IR (CH2Cl2): 1770, 1735 cm-1 ; NMR (CDCl3): δ 1.90 dd (J1 =6 Hz, J2 =7 Hz, 1H), 2.10 t (J=7 Hz, 1H), 2.13 s (3H), 2.76 bd (J=5 Hz, 2H), 2.85 dd (J 1 =2.5 Hz, J2 =15 Hz, 1H), 3.25 dd (J1 =5 Hz, J2 =15 Hz, 1H), 4.12 m (1H), 4.87 dd (J1 =6 Hz, J2 =7 Hz, 1H), 5.27 s (2H), 7.49 d (J=9 Hz, 2H), 8.25 d (J=9 Hz, 2H).

Workup

  1. filtrationfiltered through florisil
  2. customevaporated under vacuum
  3. customThe residue was chromatographed on one 15 cm×20 cm 250 micron silica gel preparative thin layer chromatography plate
  4. washwas eluted with ethyl acetate
  5. customthe eluate was evaporated under vacuum

Sources & evidence

ORD record
ord-e3ca13e595bc4ea089c816ffa4f4d6b7
Source dataset
uspto-grants-1990_01
Patent number
US04892869

Reaction notes

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