HCID 68492640, compound → HCID 59167769, compound

HRID 1616602Notes

Reaction equation

HRID 1616602 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)[N:12]=1.[H][H]>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])[N:12]=1

Participants

5

Reactant 2

HCID 68492640HCID 68492640, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59167769HCID 59167769, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

Combine 5-[4-(2-nitro-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (2.5 g, 8.2 mmol) with 5% Pd/C (300 mg) and Pd/black (50 mg) in THF and react with hydrogen (init. 39 psi) in a Parr® apparatus. When reduction is complete, filter the mixture through Celite® and concentrate the filtrate. Chromatograph the residue over silica gel (MeOH/CH2Cl2) to allow for recovery of 2.05 g (91%) of 5-[4-(2-amino-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester. MS (ES): (M+1)+ 275.1, 276.2 m/z.

Workup

  1. filtrationfilter the mixture through Celite®
  2. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-b5aeb948f77e4e9391cbcf8db6405552
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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