Hydrochloric Acid → BOC-VAL-GLY-OH

HRID 256493Notes

Reaction equation

HRID 256493 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 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.80 g of BOC-Val-Gly-OEt dissolved in 10 ml of methanol, under cooling, was added 23 ml of 1N aqueous sodium hydroxide and the mixture was stirred for one hour, followed by adjustment of pH to 8.0 with 1N hydrochloric acid. The reaction mixture was concentrated under reduced pressure to evaporate methanol, and the aqueous layer was washed with diethyl ether and then adjusted to pH 2.0 with 1N hydrochloric acid. The aqueous layer was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was treated with n-hexane and recrystallized from ethyl acetate-n-hexane to give 4.76 g (yield: 90.5%) of BOC-Val-Gly-OH melting at 101° to 107° C. Rf1 =0.20.

Workup

  1. temperatureunder cooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto evaporate methanol
  4. washthe aqueous layer was washed with diethyl ether
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous sodium sulfate
  7. concentrationfollowed by concentration under reduced pressure
  8. additionThe residue was treated with n-hexane
  9. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-5f88358dd3a34a78af180e14778f74ce
Source dataset
uspto-grants-1987_10
Patent number
US04703106

Reaction notes

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