HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → ((6R,7S)-7-tert-butoxycarbonylamino-2-fluoro-6-methyl-8-oxo-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl bromoacetate | HCID 60984 | — |
| Reactant | tert-Butyl ((2R,3S)-7-fluoro-2-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamate | HCID 67076781 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | ((6R,7S)-7-tert-butoxycarbonylamino-2-fluoro-6-methyl-8-oxo-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-acetic acid methyl ester | HCID 67076871 | 99.8% |
Reaction Steps
0.30 g (0.97 mmol) ((6R,7S)-2-Fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester in 8 ml dimethylformamide were stirred with 0.14 ml (1.45 mmol) methyl bromoacetate and 0.48 g (1.45 mmol) cesium carbonate overnight. Extraction with water/ethylacetate and chromatography on silicagel with ethylacetate/heptane 1:4 yielded 0.37 g (quant.) ((6R,7S)-7-tert-butoxycarbonylamino-2-fluoro-6-methyl-8-oxo-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-acetic acid methyl ester, MS m/e (%): 383.1 (M+H+, 14), 327.3 (24), 283.4 (199).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07211573B2 |
| Source dataset | uspto-grants-2007_05 |
| ORD ID | ord-d071088a7e2c4a6689db57eca41cabf2 |
| Source note | uspto-grants-2007_05 |