Hydrochloric Acid → N'-[1-(4-fluoro-benzoyl)-(S)-piperidine-3-carbonyl]-hydrazinecarboxylic acid-tert-butyl ester

HRID 1661179Notes

Reaction equation

HRID 1661179 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=O)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[NH:20][NH2:21].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl>ClCCl>[C:24]([O:23][C:19]([NH:20][NH:21][C:14]([C@H:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:18][CH:17]=2)[CH2:9]1)=[O:16])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 858671(3S)-1-(4-fluorobenzoyl)piperidine-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 66618300N'-[1-(4-fluoro-benzoyl)-(S)-piperidine-3-carbonyl]-hydrazinecarboxylic acid-tert-butyl esterYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-fluoro-benzoyl)-(S)-piperidine-3-carboxylic acid (1.05 g, 4.17 mmol), tert-butyl carbazate (0.55 g, 4.17 mmol), HOBT (0.562 g, 4.17 mmol), EDCI.HCl (1.2 g, 6.25 mmol) in dry dichloromethane (8 mL) was kept under stirring overnight at ambient temperature, under nitrogen atmosphere. HCl 1N (30 mL) was then added and the phases separated. The organic layer was washed with HCl 1N (30 mL), with NaOH 1N (30 mL×2 times), then with water (30 mL). Evaporation of the organic solvent afforded a crude yellow oil which was purified by flash chromatography (silica gel, eluent: DCM/MeOH 70/1) to give 0.715 g of N′-[1-(4-fluoro-benzoyl)-(S)-piperidine-3-carbonyl]-hydrazinecarboxylic acid-tert-butyl ester.

Workup

  1. customthe phases separated
  2. washThe organic layer was washed with HCl 1N (30 mL), with NaOH 1N (30 mL×2 times)
  3. customEvaporation of the organic solvent
  4. customafforded a crude yellow oil which
  5. customwas purified by flash chromatography (silica gel, eluent: DCM/MeOH 70/1)

Sources & evidence

ORD record
ord-c505bcb16a234bbd935bb0a1f8374d80
Source dataset
uspto-grants-2011_10
Patent number
US08030331B2

Reaction notes

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