(S)-Methyl 1-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoyl)pyrrolidine-2-carboxylate → Z-Val-pro-OH

HRID 1821560Notes

Reaction equation

HRID 1821560 reaction equation
[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:2]([C:6]([N:8]1[CH2:16][CH2:15][CH2:14][C@H:9]1[C:10]([O:12]C)=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4]>O.[OH-].[Na+]>[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[C@H:2]([C:6]([N:8]1[CH2:16][CH2:15][CH2:14][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 1

HCID 14032133(S)-Methyl 1-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoyl)pyrrolidine-2-carboxylate

Product 1

HCID 10783923Z-Val-pro-OH

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

3 (3.76 g, 10.4 mmol) was dissolved in 30 ml of water/acteone (1/5 v/v) and 11.4 ml NaOH (1N) was added. After completion of the reaction the organic solvent was removed by evaporation and the resulting solution was diluted by 15 ml NaHCO3 solution (saturated). Then the mixture was extracted three times by 10 ml of acetic acid ethyl ester. After that the solution was brought to pH2 by adding HCl (15% in water). The resulting mixture was extracted three times by 30 ml of acetic acid ethyl ester. The organic layer was separated and washed three times with brine, dried (Na2SO4) and evaporated.

Workup

  1. additionwas added
  2. customAfter completion of the reaction the organic solvent
  3. customwas removed by evaporation
  4. additionthe resulting solution was diluted by 15 ml NaHCO3 solution (saturated)
  5. extractionThen the mixture was extracted three times by 10 ml of acetic acid ethyl ester
  6. additionby adding HCl (15% in water)
  7. extractionThe resulting mixture was extracted three times by 30 ml of acetic acid ethyl ester
  8. customThe organic layer was separated
  9. washwashed three times with brine
  10. dry with materialdried (Na2SO4)
  11. customevaporated

Sources & evidence

ORD record
ord-ab288afb4d27438d9b1eb2f363373d9c
Source dataset
uspto-grants-2009_10
Patent number
US07608577B2

Reaction notes

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