Hydrochloric Acid → N-[(Benzyloxy)carbonyl]-L-alanyl-L-prolyl-L-proline

HRID 2413729Notes

Reaction equation

HRID 2413729 reaction equation
C[O:2][C:3](=[O:31])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:30])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:29])[C@H:16]([CH3:28])[NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].Cl>[OH-].[Na+]>[CH2:21]([O:20][C:18]([NH:17][C@H:16]([C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[C:3]([OH:31])=[O:2])=[O:30])=[O:29])[CH3:28])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53916467HCID 53916467, compound

Product 1

HCID 18611257N-[(Benzyloxy)carbonyl]-L-alanyl-L-prolyl-L-prolineYield 88.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
30 °C

Procedure

To N-benzyloxycarbonyl-L-alanyl-L-prolyl-L-proline methylester (4.31 g, 10 m mole), 1.5 N aqueous sodium hydroxide (10 ml, 15 m mole) was added and the mixture was stirred for 2 hours at 30° C. The solution was adjusted to pH 2.5 with 1N hydrochloric acid, and then extracted with two 50 ml portions of 1,2-dichloroethane. The thus obtained 1,2-dichloroethane layer was concentrated under reduced pressure. The residue was recrystallized with acetone-water to give N-benzyloxycarbonyl-L-alanyl-L-prolyl-L-proline (3.68 g).

Workup

  1. extractionextracted with two 50 ml portions of 1,2-dichloroethane
  2. concentrationThe thus obtained 1,2-dichloroethane layer was concentrated under reduced pressure
  3. customThe residue was recrystallized with acetone-water

Sources & evidence

ORD record
ord-2b9705c014f14086976cb7689f30ce9b
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

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