Nitrogen → 5-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid

HRID 2065002Notes

Reaction equation

HRID 2065002 reaction equation
N#N.C[O:4][C:5]([C:7]1[N:8]=[CH:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:13]=1)=[O:6].[Li+].[OH-]>C1COCC1.O>[C:24]([Si:21]([CH3:23])([CH3:22])[O:20][CH2:19][CH2:18][C:14]1[CH:13]=[C:12]([C:11]2[O:10][CH:9]=[N:8][C:7]=2[C:5]([OH:6])=[O:4])[CH:17]=[CH:16][CH:15]=1)([CH3:26])([CH3:25])[CH3:27]

Participants

6

Reactant 3

HCID 947NitrogenHCID 3939Lithium HydroxideHCID 669282965-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid methyl ester

Product 1

HCID 669288865-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-{3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid methyl ester (110 mg, 0.30 mmol) in THF (0.5 mL) and H2O (0.5 mL) was treated with LiOH (18 mg, 0.43 mmol). The reaction mixture was stirred at rt for 2.5 h, extracted with EA (2×5 mL), the organic layer was washed with 1N HCl (2 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=1.08 min, [M+H]+=348.40.

Workup

  1. extractionextracted with EA (2×5 mL)
  2. washthe organic layer was washed with 1N HCl (2 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8866e4346880468f83080eb8677ae77f
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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