Benzyl carbazate → tert-butyl 4-[1-(N'-benzyloxycarbonyl-hydrazinocarbonyl)-4-chlorobutan-1-yl]piperidine-1-carboxylate

HRID 546708Notes

Reaction equation

HRID 546708 reaction equation
C(N(C(C)C)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[C:25]([CH:28]([CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]1)[CH2:29][CH2:30][CH2:31][Cl:32])([OH:27])=O.[C:46]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)(=[O:49])[NH:47][NH2:48]>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:51]([O:50][C:46]([NH:47][NH:48][C:25]([CH:28]([CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]1)[CH2:29][CH2:30][CH2:31][Cl:32])=[O:27])=[O:49])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

8

Reactant 4

HCID 79242Benzyl carbazateHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 66839527Tert-butyl 4-(1-carboxy-4-chlorobutan-1-yl)piperidine-1-carboxylate

Product 1

HCID 66839389tert-butyl 4-[1-(N'-benzyloxycarbonyl-hydrazinocarbonyl)-4-chlorobutan-1-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (2.0 ml) and BOPCl (1.55 g) were added to a solution of the crude tert-butyl 4-(1-carboxy-4-chlorobutan-1-yl)piperidine-1-carboxylate (1.25 g) and benzyl carbazate (CAS No. 5331-43-1, 883 mg) in methylene chloride (15 ml), and the reaction solution was stirred at room temperature overnight. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was sequentially washed with 1 N hydrochloric acid, water, a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 928 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was sequentially washed with 1 N hydrochloric acid, water
  3. dry with materiala saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-7c15a1581fb94ba694b6275e2a199072
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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