Hydrochloric Acid → L-alanyl-D-alanine benzyl ester hydrochloride

HRID 35714Notes

Reaction equation

HRID 35714 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[C@@H:10]([CH3:24])[NH:11][C:12](=[O:23])[C@H:13]([CH3:22])[NH:14]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:26]>O1CCOCC1>[ClH:26].[CH2:1]([O:8][C:9](=[O:25])[C@@H:10]([CH3:24])[NH:11][C:12](=[O:23])[C@H:13]([CH3:22])[NH2:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13369188N-t-butoxycarbonyl-L-alanyl-D-alanine benzyl ester

Product 1

HCID 70402029L-alanyl-D-alanine benzyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a slurry of 28.7 g. of N-t-butoxycarbonyl-L-alanyl-D-alanine benzyl ester in 150 ml. of dioxane saturated with hydrogen chloride and the mixture stirred for 4 hours at room temperature. The solvent was removed in vacuo and the residue triturated with diethyl ether. The resulting solids were filtered, redissolved in methylene chloride and the solution concentrated to about 150 ml. Ether was added and the solids filtered under nitrogen, 22.0 g.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue triturated with diethyl ether
  3. filtrationThe resulting solids were filtered
  4. dissolutionredissolved in methylene chloride
  5. concentrationthe solution concentrated to about 150 ml
  6. additionEther was added
  7. filtrationthe solids filtered under nitrogen

Sources & evidence

ORD record
ord-f59d801b60d34f2d83cd8c96a4feae18
Source dataset
uspto-grants-1988_08
Patent number
US04767743

Reaction notes

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