Hydrochloric Acid → Benzyl L-valyl-L-prolinate hydrochloride

HRID 1073993Notes

Reaction equation

HRID 1073993 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:28])[C@H:16]([CH:25]([CH3:27])[CH3:26])[NH:17]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:30]>O1CCOCC1.C(OCC)C>[ClH:30].[CH2:1]([O:8][C:9](=[O:29])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:28])[C@H:16]([CH:25]([CH3:27])[CH3:26])[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14304307Boc-Val-Pro-OBzl

Product 1

HCID 14304310Benzyl L-valyl-L-prolinate hydrochlorideYield 75.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

N-t-butyloxycarbonyl-L-valyl-L-proline benzylester (16.32 g, 40 mmole) was dissolved in 4N hydrochloric acid in dioxane (100 ml) solution, and the solution was stirred for 1 hour at room temperature. The solvent was distilled off and the residue thus obtained was powdered in diethyl ether to give L-valyl-L-proline benzylester hydrochloride (yield 10.31 g, 75.6%).

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue thus obtained

Sources & evidence

ORD record
ord-33a6ac58fd3c4c7683ebad353c4f80b9
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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