1,2-Dichloroethane → N-Acetyl-tyrosinyl-valinyl-(4-phenoxy)proline Methyl Ester

HRID 862222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862222
[C:1]([NH:4][C@H:5]([C:14]([NH:16][C@H:17]([C:21]([OH:23])=O)[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[CH3:24][O:25][C:26](=[O:39])[C@@H:27]1[CH2:31][CH:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][NH:28]1.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C)C=O.C(OCC)(=O)C.ClCCl>[CH3:24][O:25][C:26](=[O:39])[C@@H:27]1[CH2:31][CH:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][N:28]1[C:21](=[O:23])[C@H:17]([CH:18]([CH3:19])[CH3:20])[NH:16][C:14](=[O:15])[C@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[NH:4][C:1](=[O:3])[CH3:2]

Komponenten

9

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22875497N-Acetyl-tyrosinyl-valineHCID 545742204-Phenoxyproline methyl ester

Produkt 1

HCID 54377655N-Acetyl-tyrosinyl-valinyl-(4-phenoxy)proline Methyl EsterAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-Acetyl-tyrosinyl-valine (0.524 g, 1.63 mmol) and 4-phenoxyproline methyl ester (0.381 g, 1.48 mmol) were dissolved in 4 ml each of dimethylformamide and dichloromethane and cooled to 0° C. To the cooled solution was added diisopropylethylamine (258 ul, 1.86 mmol), HOBT (0.24 g, 1.78 mmol), and EDC (0.37 g, 1.92 mmol) and the reaction was stirred for 18 hrs. The mixture was diluted with 400 ml of ethyl acetate and washed with water, 10% sodium hydrogen sulfate, 10% sodium bicarbonate, and water. The organic layer was concentrated to give a residue that was purified by flash chromatography (SiO2) eluting with 94:6:1 (CH2Cl2 :i-PrOH:Pyridine) to afford 360 mg of the title compound.

Aufarbeitung

  1. washwashed with water, 10% sodium hydrogen sulfate, 10% sodium bicarbonate, and water
  2. concentrationThe organic layer was concentrated
  3. customto give a residue that
  4. customwas purified by flash chromatography (SiO2)
  5. washeluting with 94:6:1 (CH2Cl2 :i-PrOH:Pyridine)

Quellen und Nachweise

ORD-Eintrag
ord-aad3e2f3a8dd4082a84dd4de5db4911c
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716929

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