Ethylmorpholine → HCID 178453396, compound

HRID 1154154Notes

Reaction equation

HRID 1154154 reaction equation
C(N1CCOCC1)C.C1CCC(N=C=N[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)CC1.[NH:24]([C:84]([O:86][CH2:87]C1C=CC=CC=1)=[O:85])[C@H:25]([C:38]([NH:40][C@H:41]([C:54]([NH:56][C@H:57]([C:70]([NH:72][C@H:73]([C:81](O)=[O:82])[CH2:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)=[O:71])[CH2:58][C:59]1[CH:64]=[CH:63][C:62]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[CH:61][CH:60]=1)=[O:55])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].[NH2:94][C@H:95]([C:103]([O:105][C:106]([CH3:109])([CH3:108])[CH3:107])=[O:104])[CH2:96][CH2:97][CH2:98][NH:99][C:100](=[NH:102])[NH2:101].Cl.C1C=C2C(N(O)N=NC2=CC=1)=O>CC(N(C)C)=O>[NH:24]([C:84]([O:86][CH2:87][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:85])[C@H:25]([C:38]([NH:40][C@H:41]([C:54]([NH:56][C@H:57]([C:70]([NH:72][C@H:73]([C:81]([NH:94][C@H:95]([C:103]([O:105][C:106]([CH3:109])([CH3:108])[CH3:107])=[O:104])[CH2:96][CH2:97][CH2:98][NH:99][C:100](=[NH:101])[NH2:102])=[O:82])[CH2:74][C:75]1[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=1)=[O:71])[CH2:58][C:59]1[CH:60]=[CH:61][C:62]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[CH:63][CH:64]=1)=[O:55])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:51])[CH3:52])=[O:48])=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 13178797HCID 13178797, compoundHCID 178451199HCID 178451199, compound

Product 1

HCID 178453396HCID 178453396, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

0.26 ml of N-ethylmorpholine and 440 mg of DCC are added at 0° C. to a solution of 1.95 g (2 mmoles) of Z-Lys(Boc)-Lys(Boc)-Tyr(But)-Phe-OH, 606 mg (2 mmoles) of H-Arg-OBut.HCl and 326 mg (2 mmoles) of HOObt in 5 ml of dimethylacetamide. The mixture is first stirred for 2 hours at 0° C. and is left to stand overnight at room temperature. On the following day the precipitate is filtered off and the filtrate is concentrated. Yield 2.5 g. The substance is purified by being recrystallized twice from ethyl acetate. Yield 1.7 g, melting point 134°-137°, [α]D26 =-26.4° (c=1, methanol).

Workup

  1. waitis left
  2. waitto stand overnight at room temperature
  3. filtrationOn the following day the precipitate is filtered off
  4. concentrationthe filtrate is concentrated
  5. customThe substance is purified
  6. customby being recrystallized twice from ethyl acetate
  7. customYield 1.7 g, melting point 134°-137°, [α]D26 =-26.4° (c=1, methanol)

Sources & evidence

ORD record
ord-721a6dd5d4b24911a71f5a1d3d9c85d5
Source dataset
uspto-grants-1984_12
Patent number
US04487764

Reaction notes

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