Hydrochloric Acid → L-prolyl-L-proline benzylester hydrochloride

HRID 1074006Notes

Reaction equation

HRID 1074006 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]1[CH2:20][CH2:19][CH2:18][N:17]1C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:30]>O1CCOCC1>[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]1[CH2:20][CH2:19][CH2:18][NH:17]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13091041Boc-prolylproline benzyl ester

Product 1

HCID 14827459L-prolyl-L-proline benzylester hydrochlorideYield 94.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-t-butyloxycarbonyl-L-prolyl-L-proline benzylester (60.70 g, 150 mmole) was dissolved in 4N hydrochloric acid in dioxane (350 ml) solution, and stirred for 1 hour at room temperature. The solution was concentrated under reduced pressure, and diethyl ether was added to the solution while cooling with ice and stirring to obtain L-prolyl-L-proline benzylester hydrochloride (47.80 g, 94.1%).

Workup

  1. concentrationThe solution was concentrated under reduced pressure, and diethyl ether
  2. additionwas added to the solution
  3. temperaturewhile cooling with ice
  4. stirringstirring

Sources & evidence

ORD record
ord-6818131225f6464592c997753d82a8fb
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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