Acetic Anhydride → HCID 12905414, compound

HRID 2049028Notes

Reaction equation

HRID 2049028 reaction equation
[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][CH:7]=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:3].[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:22]([O:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][CH:7]=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH3:3])(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 12905411HCID 12905411, compound

Product 1

HCID 12905414HCID 12905414, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

Benzyl 6-(α-Hydroxyethyl)-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylate (I) (18 mg) is dissolved in 1 ml of pyridine (Py) and 0.2 ml of acetic anhydride (Ac2O). The mixture is stirred at 25° C. for 3 hours and then evaporated to dryness to give oily residue. The residue is dissolved in 0.2 ml chloroform and chromatographed on two 20×20 cm, 250μ silica gel TLC plates (Rf 0.56, 20% ethylacetate/chloroform) to give 4 mg. of the desired product (II) which shows nmr (CDCl3, 60 MHZ) resonances at 2.02 (s, OAc), 6.48 (t, vinyl proton) and 7.40 ppm (m, aromatic protons) and ir (CHCl3) carbonyl vibrations at 1780 (β-lactam) and 1740 cm-1 (esters).

Workup

  1. customevaporated to dryness
  2. customto give oily residue
  3. customchromatographed on two 20×20 cm, 250μ silica gel TLC plates (Rf 0.56, 20% ethylacetate/chloroform)
  4. customto give 4 mg

Sources & evidence

ORD record
ord-a44acf31f84041e599f83d89067b70e4
Source dataset
uspto-grants-1980_04
Patent number
US04196211

Reaction notes

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