Hydrochloric Acid → BOC-VAL-GLY-OH

HRID 1277354Notes

Reaction equation

HRID 1277354 reaction equation
[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:6]([NH:8][CH2:9][C:10]([O:12]CC)=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].Cl>CO>[NH:1]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[C@H:2]([C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])[CH:3]([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12807303HCID 12807303, compound

Product 1

HCID 7014901BOC-VAL-GLY-OHYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

BOC-Val-Gly-OEt (10 g) was dissolved in 20 ml of methanol and 40 ml of 1 M sodium hydroxide was added thereto under cooling. The mixture was stirred with cooling for 15 minutes and at room temperature for an additional 45 minutes. The pH of the reaction mixture was adjusted to a pH of about 7 with 1 N hydrochloric acid and concentrated in vacuo. Water was then addedto the residue and the mixture was washed with diethyl ether. The pH of thewater layer was adjusted to a pH of about 2 with 1 N hydrochloric acid and the layer was extracted with ethyl acetate. The ethyl acetate layer was washed well with water, dried over magnesium sulfate and concentrated in vacuo. The resultant oily residue was solidified by addition of n-hexane and recrystallized from ethyl acetate-n-hexane to obtain 8.0 g (yield: 89%) of the desired material having a melting point of 101°-104° C.

Workup

  1. temperatureunder cooling
  2. concentrationconcentrated in vacuo
  3. washaddedto the residue and the mixture was washed with diethyl ether
  4. extractionthe layer was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed well with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. additionThe resultant oily residue was solidified by addition of n-hexane
  9. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-c75dec5c5e5d4769b219d59de50fd079
Source dataset
uspto-grants-1981_07
Patent number
US04277393

Reaction notes

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