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

HRID 546693Notes

Reaction equation

HRID 546693 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[CH2:35][CH2:34]1)[C:30]([OH:32])=O.[C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])(=[O:39])[NH:37][NH2:38]>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:25][CH2:26][CH2:27][CH2:28][CH:29]([CH:33]1[CH2:35][CH2:34]1)[C:30]([NH:38][NH:37][C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:32]

Participants

8

Reactant 4

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 668390175-Chloro-2-cyclopropyl-valeric acid

Product 1

HCID 66839486tert-butyl N'-(5-chloro-2-cyclopropyl-pentanoyl)-hydrazinecarboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (1.6 ml) and BOPCl (1.2 g) were added to a solution of the crude 5-chloro-2-cyclopropyl-valeric acid (550 mg) and tert-butyl carbazate (CAS No. 870-46-2, 555 mg) in methylene chloride (5 ml), and the reaction solution was stirred at room temperature for three 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 210 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-0d7437a33202478d846fa5da9a76a5f1
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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