Ethylmorpholine → HCID 25425656, compound

HRID 904968Notes

Reaction equation

HRID 904968 reaction equation
C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:24][C@H:25]([C:36]([O:38][CH3:39])=[O:37])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1.Cl.ON1C2C=CC=CC=2N=N1.[NH:51]([C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:60])[C@H:52]([C:56](O)=[O:57])[CH:53]([CH3:55])[CH3:54]>CN(C)C=O>[NH:51]([C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:60])[C@H:52]([C:56]([NH:24][C@H:25]([C:36]([O:38][CH3:39])=[O:37])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)=[O:57])[CH:53]([CH3:55])[CH3:54]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 25425656HCID 25425656, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

6.5 ml (approx. 50 mmoles) of N-ethylmorpholine and 11 g of dicyclohexylcarbodiimide are added at 0° C. to a solution in 100 ml of dimethylformamide of 12.64 g (50 mmoles) of H-Trp-OMe.HCl, 6.75 g (50 mmoles) of 1-hydroxybenzotriazole and 12.55 g (50 mmoles) of Z-Val-OH. The mixture is stirred for one hour at 0° C. and is allowed to stand overnight at room temperature. On the following day the precipitate is filtered off and the filtrate is stirred with 50 ml of saturated NaHCO3 solution and 1,000 ml of water. The mixture is cooled to 4° C. and the precipitate is filtered off. While still wet, the precipitate is dissolved in ethyl acetate. The ethyl acetate phase is extracted by shaking with water, saturated NaHCO3 solution, KHSO4 /K2SO4 solution and again with saturated NaHCO3 solution and is dried over Na2SO4 and concentrated to a small residue. The peptide is precipitated from the concentrated solution with petroleum ether. The precipitate is filtered off and dried. Yield 19.1 g (84%), melting point 146°-148°, [α]D22 =-13.9° (c=1, in methanol).

Workup

  1. waitto stand overnight at room temperature
  2. filtrationOn the following day the precipitate is filtered off
  3. stirringthe filtrate is stirred with 50 ml of saturated NaHCO3 solution and 1,000 ml of water
  4. temperatureThe mixture is cooled to 4° C.
  5. filtrationthe precipitate is filtered off
  6. dissolutionWhile still wet, the precipitate is dissolved in ethyl acetate
  7. extractionThe ethyl acetate phase is extracted
  8. stirringby shaking with water, saturated NaHCO3 solution, KHSO4 /K2SO4 solution and again with saturated NaHCO3 solution
  9. dry with materialis dried over Na2SO4
  10. concentrationconcentrated to a small residue
  11. customThe peptide is precipitated from the concentrated solution with petroleum ether
  12. filtrationThe precipitate is filtered off
  13. customdried
  14. customYield 19.1 g (84%), melting point 146°-148°, [α]D22 =-13.9° (c=1, in methanol)

Sources & evidence

ORD record
ord-d51e8c7798c9413bb786370271a8c8e7
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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