Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | HCID 70509211 | HCID 70509211 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 70507631 | HCID 70507631 | — |
Reaction Steps
The washed, dried methylene chloride solution of benzhydryl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate, freshly prepared according to Example 22 was cooled to -10° C. Pyridine (22 mg., 0.28 mmole), acetic anhydride (29 mg., 0.28 mmole) and 4-dimethylaminopyridine (3.4 mg., 0.028 mmoles) were added in sequence. After stirring for 1 hour at -10° C., tlc (4:1 chloroform:ethyl acetate) indicated acetylation was complete. The reaction mixture was evaporated to dryness in vacuo with toluene chases. Chromatography on silica gel using a methylene chloride-ethyl acetate gradient (0 to 7.5% ethyl acetate) afforded benzhydryl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [18 mg.; Rf 0.56 (4:1 chloroform:ethyl acetate; ir (CHCl3) 1780, 1730, 1680 cm-1 ].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04429128 |
|---|
| Source dataset | uspto-grants-1984_01 |
|---|
| ORD ID | ord-9a6b4c5d98b747a38fc06a59ff66f58d |
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| Source note | uspto-grants-1984_01 |
|---|
