Hydrochloric Acid → HCID 19790881, compound

HRID 1655757Notes

Reaction equation

HRID 1655757 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][CH2:6][NH:7][C:8](=[O:21])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])C.[OH-].[Na+].Cl>CO>[C:17]([O:16][C:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:22])=[O:3])=[O:21])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19790977HCID 19790977, compound

Product 1

HCID 19790881HCID 19790881, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.94 g of this ester were dissolved in 20 ml of methanol and, while stirring at 0°, 1 mol equivalent and after 30 minutes a further 0.2 mol equivalents of 1N sodium hydroxide solution were added. The mixture was then stirred at room temperature for one hour, 1.2 mol equivalents of 1N hydrochloric acid (PH 4) were added portionwise, the solvent was evaporated under reduced pressure and the aqueous phase was extracted several times with methylene chloride. Drying and evaporation of the extracts yielded an oily residue which crystallized upon the addition of hexane. Recrystallization from hexane yielded N-[5-(1-t-butoxyformamido)valeryl]-β-alanine in 87% yield, melting point 70°.

Workup

  1. stirringThe mixture was then stirred at room temperature for one hour
  2. customthe solvent was evaporated under reduced pressure
  3. extractionthe aqueous phase was extracted several times with methylene chloride
  4. customDrying
  5. customevaporation of the extracts
  6. customyielded an oily residue which
  7. customcrystallized upon the addition of hexane
  8. customRecrystallization from hexane

Sources & evidence

ORD record
ord-6ec717a63b614140a77fb06502e31b55
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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