Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Acetic-formic anhydride | HCID 75269 | — |
| Reactant | HCID 54433555 | HCID 54433555 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86738831 | HCID 86738831 | 94.4% |
Reaction Steps
To a cooled (ice-salt) stirred solution of 3-hydroxymethyl-4-triphenylmethylthio-2-azetidinone (1.76 g 4.7 mmol) in CH2Cl2 (10 ml) and triethylamine (2.6 g, 25 mmol) was added dropwise formic-acetic acid anhydride (1.76 g, 20 mmol). The mixture was stirred 20 min at -10° C. and 20 min at room temperature, followed by partition between water and CH2Cl2. Drying and concentration of organic phase gave an oil which crystallized from ether to give 1.7 g (94.4%) of the title compound as white solid, mp 143°-144° C.; 1Hmr (CDCl3) δ: 7.98 (1H, formyl) 7.3 (15H, s), 4.82 (1H, 4-H), 4.25 (2H, d, J=9 Hz) and 3.37 ppm (1H, m); ir (nujol) νmax : 1723, 1763, 1776 cm-1. ##STR832##
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04378314 |
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| Source dataset | uspto-grants-1983_03 |
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| ORD ID | ord-955a49c5c0ce49f398f97f9d97006e24 |
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| Source note | uspto-grants-1983_03 |
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