HCID 178470822, compound → HCID 178515456, compound

HRID 279137Notes

Reaction equation

HRID 279137 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=O)C>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl.[Zn]>[NH:20]1[CH:21]=[C:17]([C:7]23[CH2:6][CH2:5][C:4](=[O:3])[CH:15]2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8]3)[N:18]=[CH:19]1

Participants

5

Reactant 1

HCID 178470822HCID 178470822, compound

Product 1

HCID 178515456HCID 178515456, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Titanium tetrachloride (5.5 ml) was added dropwise to a stirred suspension of zinc powder (6.5 g) in dry tetrahydrofuran (300 ml) with ice cooling under a nitrogen atmosphere. The mixture was heated at reflux for one hour. 3-[2-(1H-Imidazol-4-yl)-1-oxoindan-2-yl]propionic acid ethyl ester (3.0 g) in 100 ml of dry tetrahydrofuran was then added to the refluxing mixture during 4 hours. After a further 2 hour reflux period, the reaction mixture was cooled to room temperature, quenched by cautious addition of 30 ml of methanol and the pH of the mixture was adjusted to 8-9 with aqueous sodium hydroxide solution. The slurry was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was stirred in aqueous hydrochloric acid at room temperature for 2 hours. Work-up of the reaction mixture gave the crude product, which was purified by flash chromatography using methylene chloride/methanol (97:3) as eluent. The yield was 1.2 g, m.p. 234-236° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for one hour
  3. temperatureAfter a further 2 hour reflux period
  4. customquenched by cautious addition of 30 ml of methanol
  5. filtrationThe slurry was filtered
  6. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f5d420f16cbd421cac2a5325be4613c6
Source dataset
uspto-grants-2002_03
Patent number
US06362211B1

Reaction notes

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