Triethylamine → 3-(4-Benzyloxy-phenyl)-2(S)-[(4-oxo-4H-chromene-3-carbonyl)-amino]-propionic acid methyl ester

HRID 1597467

Reaktionsgleichung

Reaktionsgleichung von HRID 1597467
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[C:3]([C:12]([OH:14])=O)=[CH:2]1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:22][O:23][C:24](=[O:42])[C@H:25]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:30][CH:29]=1)[NH2:26].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH3:22][O:23][C:24](=[O:42])[C@@H:25]([NH:26][C:12]([C:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[O:1][CH:2]=1)=[O:14])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:30][CH:29]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 181620Chromone-3-carboxylic acidHCID 12616037H-Tyr(Bzl)-OMe.HCl

Produkt 1

HCID 539568223-(4-Benzyloxy-phenyl)-2(S)-[(4-oxo-4H-chromene-3-carbonyl)-amino]-propionic acid methyl esterAusbeute 9,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a stirring solution of 360 mg (2 mmol) of chromone-3-carboxylic acid in 25 mL of CH2Cl2 at 0° C. were added several drops of DMF followed by 1 mL of 2M solution of oxalyl chloride in CH2Cl2. The resulting solution was stirred 3 h at rt and 643 mg (2 mmol) of O-benzyl-L-tyrosine methyl ester hydrochloride and 0.2 g (2.0 mmol) of triethylamine in 15 mL of CH2Cl2 were added and stirring continued overnight. Solvent was removed under reduced pressure. Product was purified by LCC on SiO2 (Hexane: EtOAc 13:7) providing 83 mg of title compound as a white solid: low resolution MS (ES+ (M+H), 458; RP-HPLC (Dynamax C-8 25 cm×4.1 mm; 50-90% CH3CN in H2O with 0.1% TFA buffer; 15 minutes; 2 mL/min): tr=10.44 min.

Aufarbeitung

  1. stirringstirring continued overnight
  2. customSolvent was removed under reduced pressure
  3. customProduct was purified by LCC on SiO2 (Hexane: EtOAc 13:7)

Quellen und Nachweise

ORD-Eintrag
ord-e12dc4bff32f48e4a04f8479379b085c
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294580B1

Verknüpfte Notizen

Wird geladen…