Pyridine → HCID 131711301, compound

HRID 1112330Notes

Reaction equation

HRID 1112330 reaction equation
[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH:25]1(N=C=NC2CCCCC2)CCCC[CH2:26]1>C(Cl)Cl.CN(C=O)C>[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH2:24]([NH-:19])[C:23]1[CH:26]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valine2×

Product 1

HCID 131711301HCID 131711301, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

When 5 is stirred with Z-Val-OH and pyridine in methylene chloride (24 hours, 20° C.), the carbonyl band at 1,888 cm-1 disappears and the polymeric activated ester 6a forms. A resin which has an identical IR spectrum can also be obtained by reacting 4 with Z-Val-OH and dicyclohexylcarbodiimide (DCC) in DMF. The dicyclohexylurea is removed by eluting with methanol. In order to determine the content of activated aminoacid ester, the resin 6a was reacted with benzylamine. From the amount of Z-L-Val-benzylamide formed, the proportion of active groups introduced is 0.15 mmole of Z-Val/g of resin. If the resin is reacted with Val-OMe in methylene chloride for 130 minutes at 20° C., the Z-dipeptide ester is again formed in a yield of 0.15 mmole/g of resin.

Workup

  1. customcan also be obtained
  2. customThe dicyclohexylurea is removed
  3. washby eluting with methanol
  4. customthe resin 6a was reacted with benzylamine

Sources & evidence

ORD record
ord-769c3e6b3bc245e5940d3f6cd589eabe
Source dataset
uspto-grants-1978_10
Patent number
US04122090

Reaction notes

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