Sodium Hydroxide → HCID 131717578, compound

HRID 466476Notes

Reaction equation

HRID 466476 reaction equation
[C:1]([CH2:3][C:4]1[C:5]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:13])([F:12])[F:11])#[N:2].[CH3:25][C:26]([CH3:33])([CH2:30][CH2:31]Br)[C:27](Cl)=[O:28].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[C:1]([C:3](=[C:27]1[C:26]([CH3:33])([CH3:25])[CH2:30][CH2:31][O:28]1)[C:4]1[C:5]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:12])([F:13])[F:11])#[N:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 19814007HCID 19814007, compoundHCID 86746207HCID 86746207, compound

Product 1

HCID 131717578HCID 131717578, compoundYield 121.8%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A 250-mL round-bottom flask equipped with a mechanical stirrer was charged with 2.0 g (5.7 mmol) 5-(cyanomethyl)-4-(2-methylpropyl)-2-(difluoromethyl)-6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester, prepared as in Example d, above, 95 mL dichloromethane, 0.12 g of benzyltriethylammonium chloride, and 2.4 g (11.3 mmol) of 2,2-dimethyl-4-bromobutyryl chloride. The solution was stirred and 24 mL 50% NaOH was added. Two additional equivalents of acid chloride were added after 15 minutes. No further progress of the reaction was noted so the solution was quenched by pouring into water and extracted with ethyl ether. The organics were washed with water, filtered, and concentrated to give 3.1 g of the desired product as a crude light brown oil. Purification by chromatography using 18% ethyl acetate in hexanes yielded 200 mg of the desired product as an oil, an 8% yield. nD25 1.4840.

Workup

  1. customA 250-mL round-bottom flask equipped with a mechanical stirrer
  2. customwas quenched
  3. additionby pouring into water
  4. extractionextracted with ethyl ether
  5. washThe organics were washed with water
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-38e7b8dbdc1f4beb826105ef34690ef0
Source dataset
uspto-grants-1992_10
Patent number
US05156670

Reaction notes

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