Hydrochloric Acid → Lithium 1-(4-cyano-3-fluorobenzyl)-imidazol-5-ylacetate

HRID 278175Notes

Reaction equation

HRID 278175 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]([O:16]C)=[O:15])=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:20])#[N:2].[Li+:21].[OH-].Cl>C1COCC1.O>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]([O-:16])=[O:15])=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:20])#[N:2].[Li+:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11108504Methyl 1-(4-cyano-3-fluorobenzyl)imidazol-5-ylacetate

Product 1

HCID 23702864Lithium 1-(4-cyano-3-fluorobenzyl)-imidazol-5-ylacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 1-(4-cyano-3-fluoro-benzyl)imidazol-5-ylacetate from Step C (260 mg, 0.95 mmol) in THF (5 mL) and water (1 mL) was added LiOH (40 mg, 0.95 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, then the solution was adjusted to pH 7 with 1 N aq. HCl and concentrated to dryness in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.

Workup

  1. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-dddc25c378a64fad8391ae1b0a381718
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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