Sodium Hydroxide → HCID 67333043, compound

HRID 1988078Notes

Reaction equation

HRID 1988078 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][CH2:5][CH:6]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:11])[CH2:7][OH:8].[OH-].[Na+]>C1COCC1.CO>[C:15]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:14]=[CH:13][C:12]([C:10]([NH:9][CH:6]([CH2:7][OH:8])[CH2:5][CH2:4][C:3]([OH:24])=[O:2])=[O:11])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67332127HCID 67332127, compound

Product 1

HCID 67333043HCID 67333043, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[(Biphenyl-4-carbonyl)-amino]-5-hydroxy-pentanoic acid methyl ester (333 mg, 1.06 mmol) in THF (10 mL) and MeOH (1.27 mL) was added to 1N NaOH (1.27 mL, 1.27 mmol, 1.2 equiv) at room temperature. The mixture was stirred for 2 hours and TLC indicated the reaction was complete. Solvent was removed and the residue was dissolved in water. After adjusting the pH to 4 with 1N HCl, solid precipitated from the solution. The solid was then collected by filtration, washed with water, and dried under vacuum overnight to afford 240 mg of 4-[(Biphenyl-4-carbonyl)-amino]-5-hydroxy-pentanoic acid in 76.7% yield. MS (ESI) m/z 314.

Workup

  1. customSolvent was removed
  2. dissolutionthe residue was dissolved in water
  3. customprecipitated from the solution
  4. filtrationThe solid was then collected by filtration
  5. washwashed with water
  6. customdried under vacuum overnight

Sources & evidence

ORD record
ord-23a89e10c248450f881fbafcc64395cb
Source dataset
uspto-grants-2009_06
Patent number
US07553873B2

Reaction notes

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