Potassium Hydroxide → Boc-D-Met-Gly-OH

HRID 746228Notes

Reaction equation

HRID 746228 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][NH:5][C:6](=[O:20])[C@@H:7]([CH2:16][CH2:17][S:18][CH3:19])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH-].[K+]>CO>[C:12]([O:11][C:9]([NH:8][C@@H:7]([C:6]([NH:5][CH2:4][C:3]([OH:21])=[O:2])=[O:20])[CH2:16][CH2:17][S:18][CH3:19])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13216971methyl Boc-D-methionyl-glycinate

Product 1

HCID 7019049Boc-D-Met-Gly-OH

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound of Example 8 (32.0 g, 0.1 mole) was dissolved in 200 ml of methanol to which was added 200 ml of 2 M potassium hydroxide. After ca. 5 min. at room temperature the solution was concentrated to about half volume and diluted with ethyl acetate. The solution was neutralized by washing with two portions of 0.5 M potassium bisulfate, and then dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was recrystallized to give the title compound, which was used in subsequent reactions without further purification.

Workup

  1. concentrationAfter ca. 5 min. at room temperature the solution was concentrated to about half volume
  2. additiondiluted with ethyl acetate
  3. washby washing with two portions of 0.5 M potassium bisulfate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was recrystallized

Sources & evidence

ORD record
ord-420658556cdf405d9fff39ed9d8c50c3
Source dataset
uspto-grants-1986_07
Patent number
US04603121

Reaction notes

Loading…