Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 3-Oxo-azetidine-1-carboxylic acid tert-butyl ester | HCID 1519404 | — |
| Reactant | HCID 178418676 | HCID 178418676 | — |
| Product | HCID 564973 | HCID 564973 | 70% |
Reaction Steps
4-Fluorophenyl magnesium bromide (6.0 mL, 1.0 solution in THF, 6 mmol) was added dropwise to a solution of 3-oxo-azetidine-1-carboxylic acid t-butyl ester (514 mg, 3 mmol) in THF (10 mL) at 0° C. The reaction mixture was stirred at 0° C. for one hour. Water was added, and the mixture was acidified with 1 N HCl solution and then extracted with ether (2×30 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a light yellow oil. This material was fractionated using preparative. HPLC. Homogeneous fractions were combined and concentrated to give the intermediate carbamate a colorless oil, (564 mg, 70% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07521442B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-aa118bcc04ce418f8948662bc6926c03 |
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| Source note | uspto-grants-2009_04 |
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