Trifluoroacetic acid → 2-{[4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phenoxy-phosphinoyloxy}-propionic Acid Ethyl Ester

HRID 33684

Reaktionsgleichung

Reaktionsgleichung von HRID 33684
[CH2:1]([O:3][C:4](=[O:42])[CH:5]([O:7][P:8]([CH2:17][C:18]([CH3:41])=[CH:19][CH2:20][C:21]1[C:22]([O:34]CC[Si](C)(C)C)=[C:23]2[C:27](=[C:28]([CH3:32])[C:29]=1[O:30][CH3:31])[CH2:26][O:25][C:24]2=[O:33])([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[CH3:6])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:42])[CH:5]([O:7][P:8]([CH2:17][C:18]([CH3:41])=[CH:19][CH2:20][C:21]1[C:22]([OH:34])=[C:23]2[C:27](=[C:28]([CH3:32])[C:29]=1[O:30][CH3:31])[CH2:26][O:25][C:24]2=[O:33])([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[CH3:6])[CH3:2]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 765462022-({4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phenoxy-phosphinoyloxy)-propionic Acid Ethyl Ester

Produkt 1

HCID 765462032-{[4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phenoxy-phosphinoyloxy}-propionic Acid Ethyl EsterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-({4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phenoxy-phosphinoyloxy)-propionic acid ethyl ester (24 mg, 0.039 mmol) in DCM (1 mL) was added TFA (0.5 mL) and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was dried under reduced pressure and the residue was purified by RP-HPLC to provide 18 mg (90%) of the desired product as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.18-1.34 (m, 3H), 1.36-1.48 (dd,3H), 2.02 (m, 3H), 2.17 (s, 3H), 2.78-2.98 (dd, 2H), 3.45 (m, 2H), 3.79 (s, 3H), 4.05-4.25 (m, 2H), 4.97 (m, 1H), 5.21 (s, 2H), 5.48 (t, J=7.2 Hz, 1H), 7.05-7.18 (m, 5H) ppm; 31P (121.4 MHz, CDCl3) δ 24.59, 26.13 ppm; MS (m/z) 517 [M−H]−, 519 [M+H]+.

Aufarbeitung

  1. customThe reaction mixture was dried under reduced pressure
  2. customthe residue was purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3d1feb5b2e8147018b8aa847e31db472
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429565B2

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