Ethanol → HCID 10314220, compound

HRID 2233536Notes

Reaction equation

HRID 2233536 reaction equation
[OH-:1].[Na+].C([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH:17]=1)[CH2:11][C@@H:12]([C:14](N)=[O:15])[NH2:13])(O)=O.[N:18]1[C:19](=[O:27])[N:20]=[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=12.[CH2:28]([OH:30])C>CO>[O:27]=[C:19]1[NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:28]([NH:13][CH:12]([CH2:11][C:10]3[CH:17]=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:14]([OH:15])=[O:1])=[O:30])=[CH:23][C:22]=2[NH:18]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86606420HCID 86606420, compound

Product 1

HCID 10314220HCID 10314220, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1M aq NaOH (0.75 mL, 0.75 mmol) was added to the methyl ester adduct of benzimidazol-2-one-5-carboxy-(L-phenylalanine)-amide (11) (65 mg, 0.1917 mmol) dissolved in methanol (7.5 mL) and this stirred overnight at room temperature. The volume was increased then increased to 50 mL by the addition of further methanol and the pH then carefully adjusted from 10 to 5 by the addition of Dowex 50 W-X8(H+) resin. The resin was rapidly filtered off, washed with further methanol (4×20 mL) and the combined filtrates rotary evaporated to dryness to give an oil. This was taken up in hot ethanol and on cooling a white solid settled out from solution. This was filtered off and dried to give benzimidazol-2-one-5-carbox-(L-phenylalanine)-amide (12) (60 mg, 97% yield) as a white powder;

Workup

  1. temperatureThe volume was increased
  2. additionthe pH then carefully adjusted from 10 to 5 by the addition of Dowex 50 W-X8(H+) resin
  3. filtrationThe resin was rapidly filtered off
  4. washwashed with further methanol (4×20 mL)
  5. customthe combined filtrates rotary evaporated to dryness
  6. customto give an oil
  7. temperatureon cooling a white solid
  8. filtrationThis was filtered off
  9. customdried

Sources & evidence

ORD record
ord-7bb95f1b2c6c4aed9afe94c4f0eb2413
Source dataset
uspto-grants-2010_05
Patent number
US07709514B2

Reaction notes

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