Hydrochloric Acid → BOC-VAL-GLY-OH

HRID 2083811Notes

Reaction equation

HRID 2083811 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 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

BOC-Val-Gly-OEt (96.8 g.) was dissolved in methanol (150 ml.) and 1 N NaOH solution (368 ml.) at -5° C. was added thereto. After 1 hour of stirring, the pH was adjusted to 8.0 by addition of 1 N HCl. Methanol was removed by concentration in vacuo and the aqueous layer was washed with ethyl ether (100 ml.). The aqueous layer was adjusted to pH 2.0 by addition of 1 N HCl. The aqueous layer was extracted four times with ethyl acetate (200 ml.), and the extract was dried using anhydrous sodium sulfate and thereafter concentrated in vacuo. The residue was treated with n-hexane and recrystallized from ethyl acetate - n-hexane to obtain BOC-Val-Gly-OH (85.5 g., Yield: 97.4%). m.p.: 112° - 117° C. (decomp.), TLC: one spot, Rf1 = 0.35.

Workup

  1. customMethanol was removed by concentration in vacuo
  2. washthe aqueous layer was washed with ethyl ether (100 ml.)
  3. additionThe aqueous layer was adjusted to pH 2.0 by addition of 1 N HCl
  4. extractionThe aqueous layer was extracted four times with ethyl acetate (200 ml.)
  5. customthe extract was dried
  6. concentrationconcentrated in vacuo
  7. additionThe residue was treated with n-hexane
  8. customrecrystallized from ethyl acetate - n-hexane

Sources & evidence

ORD record
ord-379003326c3947ddb28eaaf46b96061c
Source dataset
uspto-grants-1978_04
Patent number
US04086221

Reaction notes

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