Hydrochloric Acid → HCID 178472186, compound

HRID 1935726Notes

Reaction equation

HRID 1935726 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]2[NH:9][C:8]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:18]=1.[BH4-].[Na+].[ClH:29].C(=O)(O)[O-].[Na+]>O1CCCC1>[ClH:29].[OH:1][C:2]1[CH:3]=[C:4]([CH:19]([OH:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]2[NH:9][C:8]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178472184HCID 178472184, compound

Product 1

HCID 178472186HCID 178472186, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 3-(6-hydroxy-2-(2-phenylethyl)benzimidazol-4-yl)-3-oxopropanoate (800 mg) obtained in Inventive Example 42 in anhydrous tetrahydrofuran (16 mL), while cooling in an ice bath, was added sodium borohydride (26 mg) and the mixture was stirred at room temperature for 3 hours. The reaction solution was diluted with ice water (10 mL) and adjusted to pH 1 with 4 N hydrochloric acid. This was neutralized with saturated sodium bicarbonate aqueous solution, extracted with ethyl acetate and then washed with brine. The organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate). The desired fraction was concentrated and dissolved in hydrochloric acid/ethanol. The solvent was replaced by ether and then ether was evaporated to obtain the title compound as colorless crystal (350 mg).

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)
  7. concentrationThe desired fraction was concentrated
  8. dissolutiondissolved in hydrochloric acid/ethanol
  9. customether was evaporated

Sources & evidence

ORD record
ord-66dd71a5299c46529c1bcb9ce6a5806c
Source dataset
uspto-grants-2002_05
Patent number
US06387938B1

Reaction notes

Loading…