Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 18187448 | HCID 18187448 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 18187483 | HCID 18187483 | 55.7% |
Reaction Steps
A mixture of 1-t-butyloxycarbonyl-4-(2-phenylacetamido)acetyl-piperidine (595 mg, 1.653 mmol) and Lawesson's reagent (607 mg, 1.66 mmol) in 5 mL of toluene was heated at 120° C. for 3.5 hr. After cooling, 3:1 mixture of EtOAc and CH2Cl2 and saturated NaHCO3 solution were added and the mixture was stirred for 0.5 hr. The organic phase was separated and washed with brine. Solvent removal gave a crude product which was purified on silica gel using 2:3 mixture of EtOAc-hexane as solvent to give 330 mg of the desired product. 1H NMR (CDCl3): 1.45(9H,s); 1.58 (m, 2H), 1.95 (m, 2H), 2.74˜3.0 (m, 3H),4.2 (m, 2H) 4.4 (s, 2H). 7.46(s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06248755B1 |
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| Source dataset | uspto-grants-2001_06 |
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| ORD ID | ord-a42148aa51524822ad2247795aebd698 |
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| Source note | uspto-grants-2001_06 |
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