Ethyl Acetate → HCID 18187483, compound

HRID 1068232Notes

Reaction equation

HRID 1068232 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[CH2:15][NH:16][C:17](=O)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:36][C:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 18187448HCID 18187448, compound

Product 1

HCID 18187483HCID 18187483, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

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).

Workup

  1. temperatureAfter cooling
  2. additionwere added
  3. customThe organic phase was separated
  4. washwashed with brine
  5. customSolvent removal
  6. customgave a crude product which
  7. customwas purified on silica gel using 2:3 mixture of EtOAc-hexane as solvent

Sources & evidence

ORD record
ord-a42148aa51524822ad2247795aebd698
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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