Hydrochloric Acid → Boc-Leu-Pro-OH

HRID 435395Notes

Reaction equation

HRID 435395 reaction equation
[NH:1]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:2]([C:7]([N:9]1[CH2:23][CH2:22][CH2:21][C@H:10]1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[OH-].[Na+].Cl>CO>[NH:1]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C@H:2]([C:7]([N:9]1[CH2:23][CH2:22][CH2:21][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10093486Boc-Leu-Pro-OBn

Product 1

HCID 1798003Boc-Leu-Pro-OHYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

BOC-Leu-Pro-OBzl (82.76 g, 0.252 mM) was dissolved in methanol (600 ml). 1 N NaOH (327.6 ml, 1.3 molar excess) was added dropwise with ice cooling, and the mixture was stirred for one hour at room temperature. 1 N HCl (6 ml) was added to the reaction mixture with ice cooling, then the methanol was distilled off in vacuo. After washing the water layer with benzene and ethyl acetate, 1 N HCl (260 ml) was added with ice cooling to form an oily material which was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution and water and dried with anhydrous sodium sulfate. The solution was dried in vacuo and the residue was dissolved in benzene and lyophilized to obtain the substance [11] (58.57 g, yield: 70.8%).

Workup

  1. distillationthe methanol was distilled off in vacuo
  2. washAfter washing the water layer with benzene and ethyl acetate, 1 N HCl (260 ml)
  3. additionwas added with ice cooling
  4. customto form an oily material which
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with saturated sodium chloride solution and water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe solution was dried in vacuo
  9. dissolutionthe residue was dissolved in benzene

Sources & evidence

ORD record
ord-8daa8b039fd14b8e819f3d8540613691
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Reaction notes

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