Ethylmorpholine → HCID 131713280, compound

HRID 904959Notes

Reaction equation

HRID 904959 reaction equation
C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:24][C@H:25]([C:38]([O:40][CH3:41])=[O:39])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:29][CH:28]=1.Cl.[NH:43]([C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])[C@H:44]([C:48](O)=[O:49])[CH:45]([CH3:47])[CH3:46].ON1C2C=CC=CC=2N=N1>CN(C)C=O>[NH:43]([C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])[C@H:44]([C:48]([NH:24][C@H:25]([C:38]([O:40][CH3:41])=[O:39])[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[CH:31][CH:32]=1)=[O:49])[CH:45]([CH3:47])[CH3:46]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 6452451Methyl O-tert-butyl-L-tyrosinate hydrochloride

Product 1

HCID 131713280HCID 131713280, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

19.5 ml (approx. 150 mmoles) of N-ethylmorpholine and 33 g (160 mmoles) of DCC are added at 0° C. to a solution in 250 ml of dimethylformamide of 43.15 g (150 mmoles) of H-Tyr(But)-OMe.HCl, 37.65 g (150 mmoles) of Z-Val-OH and 20.25 g (150 mmoles) of 1-hydroxybenzotriazole. The mixture is stirred for 1 hour at 0° C. and is allowed to stand overnight at room temperature. The precipitate which has deposited is filtered off. It is rinsed with a little dimethylformamide. The filtrate is introduced into a mixture of 150 ml of saturated NaHCO3 solution and 3,000 ml of water, while stirring. The mixture is cooled to 4° C. and the precipitate is filtered off. It is washed thoroughly with water. While still wet, the product is dissolved in 400 ml of ethyl acetate. Insoluble matter is filtered off and water is separated off in a separating funnel. The ethyl acetate phase is dried over Na2SO4 and concentrated. The residue is triturated with petroleum ether and the product is filtered off. Yield 67 g (92%). Melting point 111°-112°, [α]D21 =-15.9° (c=1, methanol).

Workup

  1. waitto stand overnight at room temperature
  2. filtrationThe precipitate which has deposited is filtered off
  3. washIt is rinsed with a little dimethylformamide
  4. additionThe filtrate is introduced into a mixture of 150 ml of saturated NaHCO3 solution and 3,000 ml of water
  5. stirringwhile stirring
  6. temperatureThe mixture is cooled to 4° C.
  7. filtrationthe precipitate is filtered off
  8. washIt is washed thoroughly with water
  9. dissolutionWhile still wet, the product is dissolved in 400 ml of ethyl acetate
  10. filtrationInsoluble matter is filtered off
  11. customwater is separated off in a separating funnel
  12. dry with materialThe ethyl acetate phase is dried over Na2SO4
  13. concentrationconcentrated
  14. customThe residue is triturated with petroleum ether
  15. filtrationthe product is filtered off
  16. customMelting point 111°-112°, [α]D21 =-15.9° (c=1, methanol)

Sources & evidence

ORD record
ord-6b5403b036bc4e2e92e7e0d7941fe6f2
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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