Nitrogen → HCID 66929171, compound

HRID 2065014Notes

Reaction equation

HRID 2065014 reaction equation
N#N.C[O:4][C:5]([C:7]1[N:8]=[C:9]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:6].[Li+].[OH-].CC(=O)OCC>O1CCOCC1>[C:23]([O:22][C:20]([NH:19][CH2:18][C:9]1[O:10][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:5]([OH:6])=[O:4])[N:8]=1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 947NitrogenHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 66928527HCID 66928527, compound

Product 1

HCID 66929171HCID 66929171, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(tert-butoxycarbonylamino-methyl)-5-phenyl-oxazole-4-carboxylic acid methyl ester (200 mg, 0.60 mmol) in dioxane (2.0 mL) was treated with 1N LiOH (2.0 mL). The resulting mixture was stirred for 1 h. EA (10 mL) was added and the organic phase was washed with 1N HCl (3 mL), dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the title compound as a white solid. LC-MS-conditions 02: tR=0.89 min, [M+H]+=319.17.

Workup

  1. washthe organic phase was washed with 1N HCl (3 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3535ec76c4b54546a488a313b8130d77
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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