Sodium Hydroxide → HCID 7016051, compound

HRID 652370Notes

Reaction equation

HRID 652370 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:7]([NH:9][CH2:10][C:11]([O:13]CC)=[O:12])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[OH-].[Na+]>CO>[NH:1]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C@H:2]([C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11392924HCID 11392924, compound

Product 1

HCID 7016051HCID 7016051, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Boc-IleGly-OEt (17.4 g, 55.5 mmole) was dissolved in methanol (60 ml), and 2N NaOH (33 ml, 66.6 mmole) was added dropwise thereto while cooling and stirring. The cooling bath was removed, and the solution was stirred for 1 hour at about 15° C. and then neutralized with 6N HCl. Methanol was distilled off, and the solution was adjusted to pH~2 and extracted with ethyl acetate. The thus-obtained ethyl acetate layer was washed with water and dried with MgSO4. Ethyl acetate was distilled off therefrom,, and the thus-obtained oily residue was crystalized with ethyl acetate/n-hexane to give the object product (15.5 g, 98%).

Workup

  1. temperaturewhile cooling
  2. customThe cooling bath was removed
  3. stirringthe solution was stirred for 1 hour at about 15° C.
  4. distillationMethanol was distilled off
  5. extractionextracted with ethyl acetate
  6. washThe thus-obtained ethyl acetate layer was washed with water
  7. dry with materialdried with MgSO4
  8. distillationEthyl acetate was distilled off
  9. customthe thus-obtained oily residue was crystalized with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-a10bbdfbc15346da9e0b260d294ade6b
Source dataset
uspto-grants-1987_06
Patent number
US04670540

Reaction notes

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