Ethylmorpholine → HCID 86741769, compound

HRID 2308770Notes

Reaction equation

HRID 2308770 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:39])[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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:39])[CH2:31][N:32]([C:8](=[O:10])[C@H:2]([CH2:3][CH2:4][C:5](=[O:6])[OH:7])[NH2:1])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 33032L-Glutamic AcidHCID 86741770HCID 86741770, compound

Product 1

HCID 86741769HCID 86741769, 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 phenylglycine benzyl ester toluene sulfonic acid, neutrallized 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 added to the above reaction mixture. The reaction mixture is stirred in an ice water bath for 1 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 1 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-b837a2adadeb470a9332fd3dc2f94237
Source dataset
uspto-grants-1987_09
Patent number
US04690936

Reaction notes

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