Hydrochloric Acid → HCID 14151451, compound

HRID 868640Notes

Reaction equation

HRID 868640 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][C:10](=[O:12])[OH:11])[NH2:8].[C:22](=[O:25])(O)[O-].[Na+].Cl.[C:28]([O:31][CH2:32][CH3:33])(=[O:30])C>O.O1CCOCC1>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][C:10](=[O:11])[OH:12])[NH:8][C:22](=[O:25])[C@@H:4]([CH3:3])[NH:5][C:28]([O:31][CH2:32][C:33]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1)=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 134601AspartameHCID 516892Sodium Bicarbonate

Product 1

HCID 14151451HCID 14151451, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

In 50 ml of water were dissolved 2.4 g of α-L-aspartyl-L-phenylalanine methyl ester and 0.7 g of sodium bicarbonate. A solution of 1.9 g of N-benzyloxycarbonyl-D-alanine N-hydroxysuccinimide ester in 50 ml of dioxane was added to the solution. The mixture was stirred at room temperature for 5 hours. After the pH was adjusted to 2.5 with 6N hydrochloric acid, 150 ml of ethyl acetate was added to the mixture. The separated ethyl acetate layer was wahsed with water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Sodium sulfated was removed, and ethyl acetate was distilled off under reduced pressure. The residue was reprecipitated from ethyl acetate/hexane. Yield 2.1 g.

Workup

  1. additionwas added to the mixture
  2. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
  3. customSodium sulfated was removed
  4. distillationethyl acetate was distilled off under reduced pressure
  5. customThe residue was reprecipitated from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f70dadd6c6204f39804a8175d0ad6a1e
Source dataset
uspto-grants-1988_10
Patent number
US04780528

Reaction notes

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