Ethylmorpholine → HCID 14724727, compound

HRID 1460721Notes

Reaction equation

HRID 1460721 reaction equation
C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH:24]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C@@H:25]([C:33]([OH:35])=O)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[NH2:46][C@@H:47]([C:55]([NH:57][C@H:58]([C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH2:59][O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:56])[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:24]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C@@H:25]([C:33]([NH:46][C@@H:47]([C:55]([NH:57][C@H:58]([C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH2:59][O:60][C:61]([CH3:64])([CH3:62])[CH3:63])=[O:56])[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:35])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanineHCID 14724724HCID 14724724, compound

Product 1

HCID 14724727HCID 14724727, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4.71 ml of N-ethylmorpholine and 7.98 g of DCC are added at 0° C. to a solution of 10.69 g of Z-D-Phe-OH, 14.5 g of H-D-Phe-Ser(tBu)-OtBu.HCl and 4.89 g of HOBt in 150 ml of dimethylformamide. The mixture is left to stir at 0° C. for 1 hour and to stand at room temperature overnight. The precipitate is filtered off with suction, and the filtrate is concentrated. The residue is partitioned between ethyl acetate and water. The ethyl acetate phase is extracted by shaking successively with saturated NaHCO3 solution, KHSO4 /K2SO4 solution and water, dried over Na2SO4 and concentrated. The oil crystallizes from isopropanol/petroleum ether.

Workup

  1. waitThe mixture is left
  2. waitto stand at room temperature overnight
  3. filtrationThe precipitate is filtered off with suction
  4. concentrationthe filtrate is concentrated
  5. customThe residue is partitioned between ethyl acetate and water
  6. extractionThe ethyl acetate phase is extracted
  7. stirringby shaking successively with saturated NaHCO3 solution, KHSO4 /K2SO4 solution and water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe oil crystallizes from isopropanol/petroleum ether

Sources & evidence

ORD record
ord-bba75b66a7e74f19ab6c4a8afd6c0816
Source dataset
uspto-grants-1991_12
Patent number
US05071836

Reaction notes

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