Ethylmorpholine → HCID 178465154, compound

HRID 1075357Notes

Reaction equation

HRID 1075357 reaction equation
C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1.[NH:24]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[C@H:25]([C:28]([NH:30][C@H:31]([C:47](O)=[O:48])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:35][CH:34]=1)=[O:29])[CH2:26][OH:27].[NH2:60][C@@H:61]([C:72]([NH:74][C@H:75]([C:80]([NH:82][C@H:83]([C:91]([N:93]1[CH2:102][CH2:101][CH2:100][C@H:94]1[C:95]([NH:97][CH2:98][CH3:99])=[O:96])=[O:92])[CH2:84][CH2:85][CH2:86][NH:87][C:88](=[NH:90])[NH2:89])=[O:81])[CH2:76][CH:77]([CH3:79])[CH3:78])=[O:73])[CH2:62][CH2:63][CH2:64][C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66].Cl.Cl.ON1C(=O)C2C=CC=CC=2N=N1>CC(N(C)C)=O>[NH:24]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[C@H:25]([C:28]([NH:30][C@H:31]([C:47]([NH:60][C@@H:61]([C:72]([NH:74][C@H:75]([C:80]([NH:82][C@H:83]([C:91]([N:93]1[CH2:102][CH2:101][CH2:100][C@H:94]1[C:95]([NH:97][CH2:98][CH3:99])=[O:96])=[O:92])[CH2:84][CH2:85][CH2:86][NH:87][C:88](=[NH:89])[NH2:90])=[O:81])[CH2:76][CH:77]([CH3:79])[CH3:78])=[O:73])[CH2:62][CH2:63][CH2:64][C:65]([O:67][C:68]([CH3:69])([CH3:71])[CH3:70])=[O:66])=[O:48])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:35][CH:34]=1)=[O:29])[CH2:26][OH:27]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 73909582HCID 73909582, compoundHCID 178465159HCID 178465159, compound

Product 1

HCID 178465154HCID 178465154, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

0.26 ml of N-ethylmorpholine and 440 mg of dicyclohexylcarbodiimide are added at 0° C. to a solution of 1 g (approx. 2 mmoles) of Z-Ser-Tyr(Bzl)-OH, 1.4 g (2 mmoles) of H-D-Aad(OBut)-Leu-Arg-Pro-NH-C2H5.2HCl and 0.326 g (2 mmoles) of 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine in 8 ml of dimethylacetamide. The mixture is stirred for two hours at 0° C. and is then left to stand overnight at room temperature. The precipitate is filtered off and the filtrate is partitioned between 50 ml of n-butanol and 50 ml of saturated NaCl solution. The n-butanol phase is extracted by shaking with two 25 ml portions of saturated NaHCO3 solution and with 25 ml of water and is concentrated. The residue is triturated with ether and the product is filtered off and dried. Yield 2.05 g (94%), amorphous. [α]D22 =-37.4° (c=1, methanol).

Workup

  1. waitis then left
  2. waitto stand overnight at room temperature
  3. filtrationThe precipitate is filtered off
  4. customthe filtrate is partitioned between 50 ml of n-butanol and 50 ml of saturated NaCl solution
  5. extractionThe n-butanol phase is extracted
  6. stirringby shaking with two 25 ml portions of saturated NaHCO3 solution and with 25 ml of water
  7. concentrationis concentrated
  8. customThe residue is triturated with ether
  9. filtrationthe product is filtered off
  10. customdried
  11. custom[α]D22 =-37.4° (c=1, methanol)

Sources & evidence

ORD record
ord-e83eb93809c2494ba4f444850ff1f07a
Source dataset
uspto-grants-1983_07
Patent number
US04395400

Reaction notes

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