Ethylmorpholine → Z-Tyr(But)-Tyr(But)-Gly-OEt

HRID 1154152Notes

Reaction equation

HRID 1154152 reaction equation
C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:24][C@H:25]([C:38]([NH:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:39])[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.[NH:48]([C:65]([O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:66])[C@H:49]([C:62](O)=[O:63])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[CH:53][CH:52]=1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:48]([C:65]([O:67][CH2:68][C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1)=[O:66])[C@H:49]([C:62]([NH:24][C@H:25]([C:38]([NH:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:39])[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)=[O:63])[CH2:50][C:51]1[CH:52]=[CH:53][C:54]([O:57][C:58]([CH3:59])([CH3:61])[CH3:60])=[CH:55][CH:56]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 978520O-(1,1-Dimethylethyl)-N-((phenylmethoxy)carbonyl)-L-tyrosineHCID 131714055H-Tyr(But)-Gly-OEt.HCl

Product 1

HCID 13178773Z-Tyr(But)-Tyr(But)-Gly-OEt

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.12 ml (40 mmoles) of N-ethylmorpholine and 8.65 g (42 mmoles) of DCC are added at 0° C. to a solution of 14.35 g (40 mmoles) of H-Tyr(But)-Gly-OEt.HCl, 14.84 g (40 mmoles) of Z-Tyr(But)-OH and 5.4 g (40 mmoles) of HOBt in 100 ml of dimethylformamide. The mixture is worked up as in Example 1 a. The residue is triturated with petroleum ether. Yield 26.3 g. The substance is purified by chromatographing a solution in 9:1 methylene chloride/acetone over 150 g of silica gel. The fractions were concentrated and the residue triturated with ether. Yield 19.74 g (73%), melting point 113°, [α]D22 =-28.7° (c=1, methanol).

Workup

  1. customThe residue is triturated with petroleum ether
  2. customThe substance is purified
  3. concentrationThe fractions were concentrated
  4. customthe residue triturated with ether
  5. customYield 19.74 g (73%), melting point 113°, [α]D22 =-28.7° (c=1, methanol)

Sources & evidence

ORD record
ord-d2bd4775e00d48e2a84ab54b724b2fb5
Source dataset
uspto-grants-1984_12
Patent number
US04487764

Reaction notes

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