HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Acetate → tert-Butyl ((2S,3S)-2-methyl-4-oxoazetidin-3-yl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamate | HCID 12946603 | — |
| Catalyst | titanium(III) trichloride | HCID 10313229 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Sodium Chloride | HCID 5234 | — |
| Product | tert-Butyl ((2S,3S)-2-methyl-4-oxoazetidin-3-yl)carbamate | HCID 13155285 | 71.6% |
Reaction Steps
A solution of 4.98 g of (3S-trans)-3-t-butoxycarbonylamino-1-hydroxy-4-methylazetidinone in 200 ml of methanol was treated with 132 ml of 4.5M ammonium acetate and then 66 ml of 1.5M titanium trichloride and stirred for 4.5 hours. The aqueous solution was diluted with an equal volume of 8% sodium chloride and extracted with ethyl acetate to give 3.48 g of crude product. Recrystallization from ether-hexane yielded 3.3 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04826973 |
| Source dataset | uspto-grants-1989_05 |
| ORD ID | ord-2e46b02e4a8644fbaf9cdcbd49b9380c |
| Source note | uspto-grants-1989_05 |