HCID 22225093, compound → HCID 22225349, compound

HRID 1744800Notes

Reaction equation

HRID 1744800 reaction equation
[CH:1]([C:3]1[C:4]([NH:12][C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][CH:14]=2)=[N:5][C:6]([S:10][CH3:11])=[N:7][C:8]=1[CH3:9])=O>C1COCC1>[CH2:20]([O:19][C:17](=[O:18])/[CH:16]=[CH:1]/[C:3]1[C:4]([NH:12][C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])=[CH:15][CH:14]=2)=[N:5][C:6]([S:10][CH3:11])=[N:7][C:8]=1[CH3:9])[CH3:21]

Participants

3

Reactant 1

HCID 22225093HCID 22225093, compound

Product 1

HCID 22225349HCID 22225349, compoundYield 188.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound G (28.8 g; 0.0801 mol) and Ph3PCHCOOEt (34 g; 0.0976 mol) in 400 mL of anhydrous THF was stirred under reflux for 2 h 30′. The reaction mixture was cooled to room temperature, filtered and concentrated. The crude mixture was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=3/1 to 1/1) to yield compound H (32.5 g; 94.4%) as a yellow solid.

Workup

  1. temperatureunder reflux for 2 h 30′
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude mixture was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-f681b706565044db896c63920625592a
Source dataset
uspto-grants-2006_03
Patent number
US07019002B2

Reaction notes

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