Ethylmorpholine → HCID 86743058, compound

HRID 1762501Notes

Reaction equation

HRID 1762501 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=O)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH2:22]([O:29][C:30](=[O:37])[C@@H:31]1[CH:35]([Br:36])[CH2:34][CH2:33][NH:32]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C=O)C.ClCCl>[CH2:22]([O:29][C:30](=[O:37])[C@@H:31]1[CH:35]([Br:36])[CH2:34][CH2:33][N:32]1[C:8](=[O:10])[C@H:2]([CH2:3][CH2:4][C:5](=[O:6])[OH:7])[NH2:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 33032L-Glutamic AcidHCID 86743059HCID 86743059, compound

Product 1

HCID 86743058HCID 86743058, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A solution of 20 mmoles of pyro-L-glutamic acid and 20 mmoles of 3-bromo-proline benzyl ester toluene sulfonic acid, neutralized with N-ethyl morpholine, in dichloromethane: DMF(4:1) is cooled in an ice bath with stirring. A solution of 20 mmoles of dicyclohexylcarbodiimide in dichloromethane is ddded to the above reaction mixture. The reaction mixture is stirred in an ice water bath for one hour and then at room temperature overnight. Dicyclohexylurea is removed by filtration and the product is washed in ethyl acetate. Solvents of the combined filtrates are removed under reduced pressure with a rotary evaporator at 40° C. Ethyl acetate is added to the residue and the organic solution is washed until neutral. The organic phase is dried over anhydrous MgSO4, filtered and then the solvent is removed with a rotary evaporator. The material is crystallized from isopropanol and ether yielding the named product.

Workup

  1. temperatureis cooled in an ice bath
  2. stirringThe reaction mixture is stirred in an ice water bath for one hour
  3. customat room temperature
  4. customovernight
  5. customDicyclohexylurea is removed by filtration
  6. washthe product is washed in ethyl acetate
  7. customSolvents of the combined filtrates are removed under reduced pressure with a rotary evaporator at 40° C
  8. additionEthyl acetate is added to the residue
  9. washthe organic solution is washed until neutral
  10. dry with materialThe organic phase is dried over anhydrous MgSO4
  11. filtrationfiltered
  12. customthe solvent is removed with a rotary evaporator
  13. customThe material is crystallized from isopropanol and ether yielding the named product

Sources & evidence

ORD record
ord-ff8125bb8dfe47b29d5037a63e6e096b
Source dataset
uspto-grants-1989_05
Patent number
US04833152

Reaction notes

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