Hydrochloric Acid → HCID 13188601, compound

HRID 1590966Notes

Reaction equation

HRID 1590966 reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].Cl>C(O)C>[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13188599HCID 13188599, compound

Product 1

HCID 13188601HCID 13188601, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.3 Grams of Boc-Val-Leu-Gly-OEt was dissolved in 50 ml of ethanol. Thereto was added 20 ml of 1N aqueous sodium hydroxide solution with ice-cooling, and the mixture was stirred for 1 hour. The reaction mixture was adjusted to pH 7 with 1N hydrochloric acid and concentrated under reduced pressure. The residue was washed with diethyl ether. The aqueous layer was adjusted to pH 2 with 1N hydrochloric acid with ice-cooling and extracted with three 60-ml portions of ethyl acetate. The organic layers were combined, washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure to remove ethyl acetate. The residue was mixed with petroleum ether to crystallize the residue, whereby 5.33 g (yield: 78.4%) of the objective compound was obtained.

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. washThe residue was washed with diethyl ether
  4. temperaturecooling
  5. extractionextracted with three 60-ml portions of ethyl acetate
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationThe resulting solution was concentrated under reduced pressure
  9. customto remove ethyl acetate
  10. additionThe residue was mixed with petroleum ether
  11. customto crystallize the residue

Sources & evidence

ORD record
ord-0a416d23155e4cf189e3a3d1bcdb6350
Source dataset
uspto-grants-1993_04
Patent number
US05204326

Reaction notes

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