Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | 1,1'-(Diazomethylene)bis(benzene) | HCID 61230 | — |
| Reactant | HCID 22817349 | HCID 22817349 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86737994 | HCID 86737994 | 88.7% |
Reaction Steps
2 g (4.49 mmols) of (3S)-3-tert.-butoxycarbonylamino-(αR)-α-(4-tert.-butoxycarbonyloxyphenyl)-2-oxo-1-azetidineacetic acid are dissolved in 50 ml of dioxan and 1 g (5.2 mmols) of diphenyldiazomethane is added all at once to this solution. After 4 hours no further starting material can be seen in the TLC (CHCl3 : MeOH:HOAc, 85:12:3). The red colour is removed by adding two drops of glacial acetic acid and the mixture is evaporated in vacuo at a bath temperature of 25°. The colourless foam is dissolved in 20 ml of absolute ethanol and the product starts to crystallise out. 2.4 g (87% of theory) of pure diphenylmethyl (3S)-3-tert.-butoxycarbonylamino-(αR)-α-(4-tert.-butoxycarbonyloxyphenyl)-2-oxo-1-azetidineacetate with a melting point of 155°-157° are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04288364 |
|---|
| Source dataset | uspto-grants-1981_09 |
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| ORD ID | ord-bb1027d697d0447a95442a985c44d7af |
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| Source note | uspto-grants-1981_09 |
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