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tert-Butyl carbazate → tert-butyl N'-(5-chloro-2-cyclohexyl-pentanoyl)-hydrazinecarboxylate

HRID 546698
Notes
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Reaction equation

HRID 546698 reaction equation
C(N(C(C)C)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[Cl:25][CH2:26][CH2:27][CH2:28][CH:29]([CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C:30]([OH:32])=O.[C:39]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])(=[O:42])[NH:40][NH2:41]>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:25][CH2:26][CH2:27][CH2:28][CH:29]([CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C:30]([NH:41][NH:40][C:39]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 668392885-Chloro-2-cyclohexyl-valeric acid

Product 1

HCID 66838991tert-butyl N'-(5-chloro-2-cyclohexyl-pentanoyl)-hydrazinecarboxylateYield 36%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

IPEA (0.68 ml) and BOPCl (496 mg) were added to a solution of 5-chloro-2-cyclohexyl-valeric acid (285 mg) and tert-butyl carbazate (215 mg) in methylene chloride (2.5 ml), and the reaction solution was stirred at room temperature for 5.5 hours. 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 156 mg of the title compound. The property values of the compound are 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-10ef11424869495dae2302208e269ed1
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935815B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes