Water → HCID 67100075, compound

HRID 1868920Notes

Reaction equation

HRID 1868920 reaction equation
CC(C)([O-])C.[K+].F[C:8]1[CH:26]=[N:25][CH:24]=[CH:23][C:9]=1[C:10]([CH:12]([C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:11].O>CN1C(=O)CCC1>[OH:11][C:10]1[C:9]2[CH:23]=[CH:24][N:25]=[CH:26][C:8]=2[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 67099491HCID 67099491, compound

Product 1

HCID 67100075HCID 67100075, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A mixture of potassium t-butoxide (0.34 g, 3.0 mmol) in 8 mL NMP stirred at room temperature was treated with a solution of ethyl 2-(3-fluoroisonicotinoyl)-4-methyl-3-oxopentanoate (0.28 g, 1.00 mmol) in 1 mL NMP drop wise. The dark red solution was stirred at room temperature for 15 hours, M+1=262. There were two spots that had the MS=262. The mixture was poured into 200 mL water. The mixture was extracted with DCM (3×50 mL). The combined organic layers were washed with brine (20 mL), dried, and concentrated. The crude product was purified by column eluting with 10-50% EtOAc/hexane to give 0.2 g oil. MS m/e: (M+H)+ 262.

Workup

  1. stirringThe dark red solution was stirred at room temperature for 15 hours
  2. extractionThe mixture was extracted with DCM (3×50 mL)
  3. washThe combined organic layers were washed with brine (20 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by column
  7. washeluting with 10-50% EtOAc/hexane

Sources & evidence

ORD record
ord-a8abad14a5914fd4bfa39267547bb259
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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