Phenyl chloroformate → HCID 54521784, compound

HRID 2296682Notes

Reaction equation

HRID 2296682 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:22][C:21]([S:23]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][C@@H:27]3[C:32]([NH:34][O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)=[O:33])(=[O:25])=[O:24])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[S:22][C:21]([S:23]([N:26]3[CH2:31][CH2:30][N:29]([C:2]([O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[O:3])[CH2:28][C@@H:27]3[C:32]([NH:34][O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)=[O:33])(=[O:24])=[O:25])=[CH:20][CH:19]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 53817994HCID 53817994, compound

Product 1

HCID 54521784HCID 54521784, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

Phenyl chloroformate (60 mg) in CHCl3 (1 ml) was added to (2R)-1-[5-(4-Fluorophenyl)thiophene-2-sulfonyl]-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide (150 mg) in pyridine (0.5 ml) and CHCl3 (0.5 ml) dropwise with cooling on an ice bath. The reaction mixture was stirred at said temperature for 2 hours. The mixture was concentrated in vacuo, and the residue was partitioned between AcOEt and 5% aqueous citric acid. The organic layer was washed with 5% aqueous citric acid, saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution, dried over MgSO4, and concentrated in vacuo to give 202 mg of (2R)-1-[5-(4-fluorophenyl)thiophene-2-sulfonyl]-4-phenoxycarbonyl-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide.

Workup

  1. temperaturewith cooling on an ice bath
  2. customfor 2 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was partitioned between AcOEt and 5% aqueous citric acid
  5. washThe organic layer was washed with 5% aqueous citric acid, saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d07a9dc70cf5406caeb9129bcc5933cc
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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