1-Isopropylhydrazine hydrochloride → HCID 131736506, compound

HRID 1478221Notes

Reaction equation

HRID 1478221 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]([C:24](=O)[CH3:25])[C:20](OC)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[CH:28]([NH:31][NH2:32])([CH3:30])[CH3:29]>Cl.C(O)C.CC(O)C.O>[CH:28]([N:31]1[C:20](=[O:21])[C:19]([NH:18][C:16](=[O:17])[O:15][CH2:14][CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[C:24]([CH3:25])[NH:32]1)([CH3:30])[CH3:29]

Participants

7

Reactant 2

HCID 855731-Isopropylhydrazine hydrochlorideHCID 118511072HCID 118511072, compound

Product 1

HCID 131736506HCID 131736506, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-oxobutanoate (2.766 g, 7.83 mmol) in 1.25M HCl in ethanol (25 mL) was added isopropylhydrazine hydrochloride (1.298 g, 11.74 mmol). The reaction mixture was stirred at reflux. Upon completion the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography using a gradient of 0-100% EtOAc in iso-hexane and 10% MeOH in EtOAc afforded crude material. The crude material was dissolved in IPA to which water was added to give a cloudy mixture that was sonicated and left to stand at room temperature. The resulting suspension was filtered and the solid dried under reduced pressure to afford the title compound;

Workup

  1. temperatureat reflux
  2. customthe solvent was removed under reduced pressure
  3. customThe crude material was adsorbed onto silica and purification by chromatography
  4. customafforded crude material
  5. additionwas added
  6. customto give a cloudy mixture that
  7. customwas sonicated
  8. waitleft
  9. customto stand at room temperature
  10. filtrationThe resulting suspension was filtered
  11. customthe solid dried under reduced pressure

Sources & evidence

ORD record
ord-663a0c15d98b4b37b2752fa8ccb55ca0
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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