Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Methanesulfonate | HCID 85257 | — |
| Reactant | (2R,3S)-3-PHENYLISOSERINE ETHYLESTER | HCID 9883276 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 9900773 | HCID 9900773 | — |
Reaction Steps
In a 100 ml flask containing a solution of (2R,3S)-N-benzoyl-3-phenylisoserine ethyl ester (2.00 g, 6.38 mmol) in pyridine (20 ml) at 0° C. was added methanesulfonyl chloride (0.52 ml, 6.70 mmol) dropwise over a 2 minute period. The solution was stirred at 0 to 4° C. for 90 minutes and then at 65-70° C. for 18 hours. (The reaction was monitored by TLC using 1:2 EtOAc:Toluene as eluent, Rf for the starting material =0.42, Rf for the mesylate=0.48 and Rf for the cis-oxazoline title product =0.78, UV visualization.)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06090951 |
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| Source dataset | uspto-grants-2000_07 |
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| ORD ID | ord-752ee54afb8f4e08ad6d2cb2f49cd358 |
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| Source note | uspto-grants-2000_07 |
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