Nitrogen → HCID 178455423, compound

HRID 2065010Notes

Reaction equation

HRID 2065010 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]([C:18]([CH3:26])([CH3:25])[O:19][SiH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:13]=1)=[O:6].C1COCC1.O.[OH-].[Li+]>CC(=O)OCC.O>[C:21]([SiH2:20][O:19][C:18]([CH3:26])([CH3:25])[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)([CH3:24])([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 131730002HCID 131730002, compound

Product 1

HCID 178455423HCID 178455423, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-[3-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-oxazole-4-carboxylic acid methyl ester (673 mg, 1.94 mmol) in 1:1 THF:H2O (6.4 mL) was treated with lithium hydroxide monohydrate (115 mg, 2.71 mmol). The resulting mixture was stirred for 2.5 h. EA (20 mL) was added and the organic phase was washed with 1N HCl (10 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=1.07 min, [M+H]+=334.13.

Workup

  1. washthe organic phase was washed with 1N HCl (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-9380af88dd85424da349469f533d653a
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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