Diphosgene → HCID 86700674, compound

HRID 1406859Notes

Reaction equation

HRID 1406859 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)[Cl:5].[CH2:9]([O:16][NH:17][C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31]2[N:35]=[CH:34][O:33][N:32]=2)[CH2:20][CH2:19]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[CH2:9]([O:16][N:17]([C:4]([Cl:5])=[O:3])[C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31]2[N:35]=[CH:34][O:33][N:32]=2)[CH2:20][CH2:19]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 86700673HCID 86700673, compound

Product 1

HCID 86700674HCID 86700674, compoundYield 183.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (405 mg, 4.0 mmol) and diphosgene (514 mg, 2.6 mmol) were added to a solution of (2S,5R)-tert-butyl 5-(benzyloxyamino)-2-(1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (750 mg, 2.0 mmol) in DCM (70 mL). The mixture was stiffed at 0° C. for 3 hrs. Then, the reaction mixture was washed with saturated sodium chloride (2×), dried over Na2SO4, and concentrated to give (2S,5R)-tert-butyl 5-(benzyloxy(chlorocarbonyl)amino)-2-(1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (1.6 g), which was used directly in the next step. ESI-MS (EI+, m/z): 437[M+H]+.

Workup

  1. washThen, the reaction mixture was washed with saturated sodium chloride (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-74bef95766234d3aba16b6029e8398e1
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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