Ethylmorpholine → Z-Tyr(But)-Phe-OMe

HRID 1154153Notes

Reaction equation

HRID 1154153 reaction equation
C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1.[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.[NH2:51][C@H:52]([C:60]([O:62][CH3:63])=[O:61])[CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.Cl.C1C=CC2N(O)N=NC=2C=1>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:51][C@H:52]([C:60]([O:62][CH3:63])=[O:61])[CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:40])[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[CH:31][CH:32]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 978520O-(1,1-Dimethylethyl)-N-((phenylmethoxy)carbonyl)-L-tyrosine

Product 1

HCID 13178789Z-Tyr(But)-Phe-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

13 ml of N-ethylmorpholine and 22 g of DCC are added at 0° C. to a solution of 40.7 g (0.1 mmole) of Z-Tyr(But)-OH, 21.6 g of H-Phe-OMe hydrochloride and 13.5 g (0.1 mmole) of HOBt in 200 ml of dimethylformamide. The mixture is worked up as in the case of Example 1 a. The residue is triturated with petroleum ether and suction-drained. Yield 50.3 g (94%), melting point 103°-104° C., [α]D24 =-12.3° (c=1, methanol).

Workup

  1. customThe residue is triturated with petroleum ether
  2. customYield 50.3 g (94%), melting point 103°-104° C., [α]D24 =-12.3° (c=1, methanol)

Sources & evidence

ORD record
ord-562cb76d7f5240d1945f86ee86848e4f
Source dataset
uspto-grants-1984_12
Patent number
US04487764

Reaction notes

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