Methanol → HCID 54253916, compound

HRID 393482Notes

Reaction equation

HRID 393482 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1)[N:5]([C:7]([C:9]1([CH2:14][CH2:15][O:16][CH3:17])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8])[CH3:6].[Cl-].[NH4+].CO>[Zn].O>[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=1)[N:5]([CH3:6])[C:7]([C:9]1([CH2:14][CH2:15][O:16][CH3:17])[CH2:10][CH2:11][CH2:12][CH2:13]1)=[O:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 59072630HCID 59072630, compound

Product 1

HCID 54253916HCID 54253916, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-N-methyl-4-nitro-L-phenylalanine methyl ester (1.35 mmol, 530 mg), zinc dust (˜325 mesh, 13.5 mmol, 0.88 g, 10 equiv.) and ammonium chloride (20.2 mmol, 1.08 g, 15 equiv.) was added methanol (10 mL) and water (5 mL) at room temperature. After addition of water, the reaction was exothermic. The suspension was stirred for 2 h at room temperature at which time TLC analysis of the mixture indicated the absence of starting material, the reaction mixture was filtered through a pad of celite and the filter cake was washed with methanol (50 mL) and water (40 mL). The mixture was concentrated and extracted with ethyl acetate (3×30 mL). The combined extracts were washed with brine solution (30 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent afforded 490 mg (100%) of a yellow oil. HR MS (C20H30N2O4): Obs. mass,362.2202. Calcd. mass, 362.2206 (M+).

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite
  2. washthe filter cake was washed with methanol (50 mL) and water (40 mL)
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washThe combined extracts were washed with brine solution (30 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationFiltration of the drying agent and concentration of the solvent

Sources & evidence

ORD record
ord-d33f173b45ed4d14818710f8125c7d24
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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