Vinyl Acetate → HCID 131715756, compound

HRID 847203Notes

Reaction equation

HRID 847203 reaction equation
[N:1]([C:4]1[CH2:5][C@@H:6]2[CH2:20][C:19](=[O:21])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=[N+]=[N-].[C:22]([O:25][CH:26]=[CH2:27])(=[O:24])[CH3:23].C(=O)(O)[O-].[Na+]>ClCCl>[C:22]([O:25][CH:26]1[CH2:27][N:1]1[C:4]1[CH2:5][C@@H:6]2[CH2:20][C:19](=[O:21])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7904Vinyl AcetateHCID 516892Sodium BicarbonateHCID 131715738HCID 131715738, compound

Product 1

HCID 131715756HCID 131715756, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl 2-azido-carbapen-2-em-3-carboxylate (5.3 mg, 19 micromol) and vinyl acetate (100 microliter) in dry dichloromethane (200 microliter) was treated with excess sodium bicarbonate and kept 3 days at ambient temperature. The mixture was filtered through florisil, the florisil was washed with ethyl acetate (25 ml), and the combined filtrate and wash was evaporated under vacuum. The residue was chromatographed on one 20 cm ×20 cm 250 micron silica gel preparative thin layer chromatography plate developed with 9:1 (v/v) diethyl ether-ethyl acetate. Product was eluted with ethyl acetate and the eluate evaporated under vacuum to provide 1.2 mg (19%) benzyl 2-(2-acetoxyaziridin-1-yl)-carbapen-2-em-3-carboxylate; IR (CH2Cl2) 1770, 1735 cm-1 ; NMR (CDCl3): δ 1.92 bt (J=6.5 Hz, 1H), 2.08 t (J=7 Hz, 1H), 2.13 s (3H), 2.70 dd (J, 6 Hz, J2 =17 Hz, 1H), 2.76 dd (J1 =6 Hz, J2 =17 Hz, 1H), 2.86 dd (J1 =2 Hz, J2 =15 Hz, 1H), 3.24 dd (J1 =5 Hz, J2 =15 Hz, 1H), 4.16 m (1H), 4.79 bt (J=7 Hz, 1H), 5.17 s (2H), 7.37 m (5H).

Workup

  1. filtrationThe mixture was filtered through florisil
  2. washthe florisil was washed with ethyl acetate (25 ml)
  3. washthe combined filtrate and wash
  4. customwas evaporated under vacuum
  5. customThe residue was chromatographed on one 20 cm ×20 cm 250 micron silica gel preparative thin layer chromatography plate
  6. washProduct was eluted with ethyl acetate
  7. customthe eluate evaporated under vacuum

Sources & evidence

ORD record
ord-93cca8eb5b80454d88328b8dadf68466
Source dataset
uspto-grants-1992_08
Patent number
US05140030

Reaction notes

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