HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Hydroxide → Oxazoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | 4-Fluorobenzaldehyde | HCID 68023 | — |
| Reactant | 4-Methylpiperidine | HCID 69381 | — |
| Reactant | Methyl isocyanoacetate | HCID 547815 | — |
| Reactant | Potassium | HCID 5462222 | — |
| Reactant | Edci hobt | HCID 18410139 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Oxazoline | HCID 68157 | — |
| Product | Oxazoline amide | HCID 22575031 | — |
Reaction Steps
Compound 10 (Reaction Scheme 4) was obtained in three synthetic steps. Methyl 2-isocyanoacetate reacted with 4-fluorobenzaldehyde and KOH in MeOH for 7 h at room temperature to afford diastereoselectivity and quantitatively the crude potassium salt trans-ANP 20162. Potassium salt ANP 20162 was coupled with 4-methylpiperidine using the EDCI-HOBT method in dichloromethane to produce the oxazoline amide, LPO 26074 Oxazoline LPO 26074 then underwent ring opening using a HCl 37% solution in MeOH at 45° C. for 15 min to give Compound 10 in 7% yield after purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08168631B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-3c09a4313d91486682cedb1c0d5f0e64 |
| Source note | uspto-grants-2012_05 |