4-Methylmorpholine → Z-Phe-D-Trp-OMe

HRID 743144Notes

Reaction equation

HRID 743144 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:23][C@@H:24]([C:35]([O:37][CH3:38])=[O:36])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1.Cl.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C1COCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:23][C@@H:24]([C:35]([O:37][CH3:38])=[O:36])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 757711-HydroxybenzotriazoleHCID 11448200methyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 15755276Z-Phe-D-Trp-OMeYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.60 g (2 mmol) of Z-Phe-OH, 0.51 g (2 mmol) of H-D-Trp-OMe.HCl, 0.46 g (2.4 mmol) of EDCI, 0.32 g (2.4 mmol) of HOBT and 0.44 ml (4 mmol) of NMM are dissolved at -10° C. in 10 ml THF and stirred at room temperature for 15 hours. The THF is distilled off under vacuum, the residue dissolved in 50 ml ethyl acetate and the organic phase washed three times with 10 ml 0.5 N HCl, 10% NaHCO3 solution and water respectively. The organic phase is dried with MgSO4 and the solvent distilled off under vacuum. 0.48 g (48%) of thin-layer chromatographically identical Z-Phe-D-Trp-OMe are obtained as a colourless powder.

Workup

  1. distillationThe THF is distilled off under vacuum
  2. dissolutionthe residue dissolved in 50 ml ethyl acetate
  3. washthe organic phase washed three times with 10 ml 0.5 N HCl, 10% NaHCO3 solution and water respectively
  4. dry with materialThe organic phase is dried with MgSO4
  5. distillationthe solvent distilled off under vacuum

Sources & evidence

ORD record
ord-b124a6c7295e4cb596a9cfda04a9d825
Source dataset
uspto-grants-1996_09
Patent number
US05556836

Reaction notes

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