Isopropenyl acetate → p-Nitrobenzyl 2-(2-acetoxy-2-methylaziridin-1-yl)carbapen-2-em-3-carboxylate

HRID 847201Notes

Reaction equation

HRID 847201 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][C:29]([CH3:31])=[CH2:30])(=[O:27])[CH3:26]>ClCCl>[C:25]([O:28][C:29]1([CH3:31])[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

4

Reactant 2

HCID 7916Isopropenyl acetateHCID 131715741p-Nitrobenzyl 2-azidocarbapen-2-em-3-carboxylate

Product 1

HCID 131715748p-Nitrobenzyl 2-(2-acetoxy-2-methylaziridin-1-yl)carbapen-2-em-3-carboxylateYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Two solutions of p-nitrobenzyl 2-azidocarbapen-2-em-3-carboxylate (52 mg and 24 mg, 231 micromol) and 2-acetoxy-1-propene (0.25 ml each) in dichloromethane were kept 2.5 days at ambient temperature. The mixtures were combined, filtered through florisil, and evaporated under vacuum. The residue was chromatographed on four 20 cm×20 cm 250 micron silica gel preparative thin layer chromatography plates developed with 5:1 (v/v) diethyl ether-ethyl acetate. The band centered at Rf 0.25 was eluted with ethyl acetate and the eluate evaporated under vacuum to provide 15.9 mg (17%) p-nitrobenzyl 2-(2-acetoxy-2-methylaziridin-1-yl)carbapen-2-em-3-carboxylate; IR (CH2Cl2): 1770, 1735 cm-1, NMR (CDCl3): δ 1.69 s (3H), 2.11 s (3H), 2.16 d (J=7 Hz, 1H), 2.22 d (J=7Hz, 1H), 2.74 dd (J=8 Hz, J2 =17 Hz, 1H), 2.79 dd (J1 =3 Hz, J2 =16 Hz, 1H), 2.84 dd (J1 =5 Hz, J2 =17 Hz, 1H), 3.21 dd (J1 =6 Hz, J2 =16 Hz, 1H), 4.30 m (1H), 5.29 d (J=12 Hz, 1H), 5.35 d (J=12 Hz, 1H), 7.57 d (J=9 Hz, 2H), 8.29 d (J=9 Hz, 2H); MS (m/e): 402 (M+), 359, 342, 316, 300, 274, 258, 222.

Workup

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

Sources & evidence

ORD record
ord-18bee056937e402cb64c419a551522e7
Source dataset
uspto-grants-1992_08
Patent number
US05140030

Reaction notes

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