Ethylmorpholine → Z-Tyr(But)-NH-C2H5

HRID 904971Notes

Reaction equation

HRID 904971 reaction equation
[CH2:1]([N:3]1CCOCC1)[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH:24]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:25]([C:38]([OH:40])=O)[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.C(N)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[NH:24]([C:41]([O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:42])[C@H:25]([C:38]([NH:3][CH2:1][CH3:2])=[O:40])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 978520O-(1,1-Dimethylethyl)-N-((phenylmethoxy)carbonyl)-L-tyrosine

Product 1

HCID 131713304Z-Tyr(But)-NH-C2H5

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3.2 ml (25 mmoles) of N-ethylmorpholine and 5.56 g (27 mmoles) of dicyclohexylcarbodiimide are added at 0° C. to a solution in 50 ml of dimethylformamide of 9.27 g (25 mmoles) of Z-Tyr(But)-OH, 2.03 g (25 mmoles) of ethylamine hydrochloride and 3.38 g of 1-hydroxybenzotriazole. The mixture is stirred for two hours at 0° C. and for 5 hours at room temperature and is left to stand overnight at room temperature. The precipitate is filtered off and the filtrate is concentrated. The resulting oil is partitioned between ethyl acetate and water. The ethyl acetate phase is extracted by shaking with KHSO4 solution, NaHCO3 solution and water, is dried over Na2SO4 and is concentrated. The residue cyrstallizes from petroleum ether. Yield 9.63 g (96% ), melting point 107°-110°, [α]D22 =-0.5° (c=1, methanol).

Workup

  1. waitis left
  2. waitto stand overnight at room temperature
  3. filtrationThe precipitate is filtered off
  4. concentrationthe filtrate is concentrated
  5. customThe resulting oil is partitioned between ethyl acetate and water
  6. extractionThe ethyl acetate phase is extracted
  7. stirringby shaking with KHSO4 solution, NaHCO3 solution and water
  8. dry with materialis dried over Na2SO4
  9. concentrationis concentrated
  10. customYield 9.63 g (96% ), melting point 107°-110°, [α]D22 =-0.5° (c=1, methanol)

Sources & evidence

ORD record
ord-2a09d53a72fd48b1bf7da69b3c192c25
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

Loading…