Z-Ala-gln-OH → L-Alanyl-L-Glutamine

HRID 1086941

Reaction equation

HRID 1086941 reaction equation
C([NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:23]([OH:25])=[O:24])[CH2:18][CH2:19][C:20](=[O:22])[NH2:21])=[O:15])[CH3:13])(OCC1C=CC=CC=1)=O.[H][H]>CO.O.[C].[Pd]>[NH2:11][C@H:12]([C:14]([NH:16][C@H:17]([C:23]([OH:25])=[O:24])[CH2:18][CH2:19][C:20](=[O:22])[NH2:21])=[O:15])[CH3:13]

Participants

6

Reactant 2

HCID 14534789Z-Ala-gln-OHHCID 178418361HCID 178418361, compound

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 90.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Into a 200 ml three-necked flask was charged 5.0 g (14.2 mmol) of Z-L-Ala-L-Gln, and the peptide was dissolved in 100 ml of a mixture of methanol and water (methanol:water =7:3) and stirred with a magnetic stirrer. After the air in the flask had been replaced with nitrogen, 0.8 g of 2% by weight of palladium-carbon was added thereto, and the protective group was eliminated in a stream of hydrogen. After 2 hours, the completion of the reaction was confirmed by thin layer chromatography, and then the palladium-carbon was filtered off. The filtrate was concentrated to 20 ml under reduced pressure, and 40 ml of isopropyl alcohol was added thereto. The resulting mixture was stirred for 30 minutes, during which time crystals precipitated. The crystals were collected by filtration, washed with isopropyl alcohol and then dried under reduced pressure to give 2.8 g (12.9 mmol) (90%) of L-Ala-L-Gln.

Workup

  1. additionwas added
  2. filtrationthe palladium-carbon was filtered off
  3. concentrationThe filtrate was concentrated to 20 ml under reduced pressure, and 40 ml of isopropyl alcohol
  4. additionwas added
  5. stirringThe resulting mixture was stirred for 30 minutes, during which time crystals
  6. customprecipitated
  7. filtrationThe crystals were collected by filtration
  8. washwashed with isopropyl alcohol
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-60edb0568624431aa3dd8c20db345199
Source dataset
uspto-grants-1991_07
Patent number
US05032675

Linked notes

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