Hydrazine hydrate (1:1) → HCID 57991899, compound

HRID 2075399Notes

Reaction equation

HRID 2075399 reaction equation
O.[NH2:2][NH2:3].[O:4]=[C:5]1[CH2:9][CH2:8][C@H:7]([CH2:10][C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[N:6]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[NH4+].[Cl-]>C1COCC1>[C:24]([O:23][C:21]([NH:6][C@@H:7]([CH2:10][C:11]1[CH:12]=[N:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=1)[CH2:8][CH2:9][C:5]([NH:2][NH2:3])=[O:4])=[O:22])([CH3:25])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 25517Ammonium ChlorideHCID 57950517HCID 57950517, compound

Product 1

HCID 57991899HCID 57991899, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrazine monohydrate (0.93 mL, 18.6 mmol) was added to a solution of (R)-tert-butyl 2-oxo-5-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (1.6 g, 4.65 mmol) in THF (23 mL), and the mixture was stirred at room temperature for 1 hour. Saturated aqueous NH4Cl (20 mL) was added and the mixture was extracted with EtOAc (3×20 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting off-white solid was purified by recrystallization from EtOAc to provide (R)-4-(tert-butoxycarbonylamino)-5-(6-(trifluoromethyl)pyridin-3-yl)pentanehydrazide (1.40 g, 80%) as a white solid. LCMS (API-ES) m/z: 399.1 (M+Na+).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting off-white solid was purified by recrystallization from EtOAc

Sources & evidence

ORD record
ord-adeefeee63c64a1489e722d40ef904cc
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

Loading…