HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 1-(1-Hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Acetic acid, 2-oxo-, methyl ester | HCID 70205 | — |
| Reactant | 3-(Triphenylmethylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one | HCID 21519177 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | 1-(1-Hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one | HCID 53714964 | 64% |
Reaction Steps
3-(Triphenylmethylamino)-4-(3-phenylprop-2-ynylthio) azetidin-2-one (526mg) and methyl glyoxylate (1.17g) were refluxed in dry benzene (25ml) with provision for the removal of water. After 11/2 hours the solvent was evaporated and the residue was chromatographed on silica to give 1-(1-hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one as an amorphous solid (399 mg). νmax (CHCl3) 3475 (--OH), 1770 (β-lactam), 1750 (ester) cm-1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US03939157 |
| Source dataset | uspto-grants-1976_02 |
| ORD ID | ord-3cc90c8cd3aa4749b64a735c745c1059 |
| Source note | uspto-grants-1976_02 |