Nitrogen → HCID 67128604, compound

HRID 1189367Notes

Reaction equation

HRID 1189367 reaction equation
N#N.C[O:4][C:5]([C:7]1[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([F:19])([F:18])[CH3:17])[O:10][CH:11]=1)=[O:6].[OH-].[Na+]>C1COCC1.Cl>[F:19][C:16]([F:18])([CH3:17])[CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[O:10][CH:11]=[C:7]([C:5]([OH:6])=[O:4])[N:8]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 67128576HCID 67128576, compound

Product 1

HCID 67128604HCID 67128604, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(5,5-difluoro-hexyl)-oxazole-4-carboxylic acid methyl ester (320 mg, 1.29 mmol) in THF (13 mL) was treated at rt with 1N NaOH (6.5 mL, 6.5 mmol) and the reaction mixture was stirred for 1.5 h at rt. The reaction mixture was poured in 1N HCl (13 mL) and extracted twice with EA (2×20 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a brown solid. LC-MS-conditions 02: tR=0.84 min, [M+H]+=234.45.

Workup

  1. extractionextracted twice with EA (2×20 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-803306675ed84406b799d2f08c278a18
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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