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2-[Hydroxy-(2-{4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enylamino}-ethyl)-phosphinoyloxy]-propionic acid ethyl ester → 2-(Hydroxy-{2-[4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enylamino]-ethyl}-phosphinoyloxy)-propionic Acid

HRID 272179
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 272179
C([O:3][C:4](=[O:39])[CH:5]([O:7][P:8]([OH:38])([CH2:10][CH2:11][NH:12][CH2:13][C:14]([CH3:37])=[CH:15][CH2:16][C:17]1[C:18]([O:30]CC[Si](C)(C)C)=[C:19]2[C:23](=[C:24]([CH3:28])[C:25]=1[O:26][CH3:27])[CH2:22][O:21][C:20]2=[O:29])=[O:9])[CH3:6])C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[OH:38][P:8]([CH2:10][CH2:11][NH:12][CH2:13][C:14]([CH3:37])=[CH:15][CH2:16][C:17]1[C:18]([OH:30])=[C:19]2[C:23](=[C:24]([CH3:28])[C:25]=1[O:26][CH3:27])[CH2:22][O:21][C:20]2=[O:29])([O:7][CH:5]([CH3:6])[C:4]([OH:39])=[O:3])=[O:9]
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Komponenten

3

Edukt 1

HCID 765410322-[Hydroxy-(2-{4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enylamino}-ethyl)-phosphinoyloxy]-propionic acid ethyl ester

Produkt 1

HCID 725636812-(Hydroxy-{2-[4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enylamino]-ethyl}-phosphinoyloxy)-propionic AcidAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chloride
Lösungsmittel

Versuchsvorschrift

A solution of 2-[hydroxy-(2-{4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enylamino}-ethyl)-phosphinoyloxy]-propionic acid ethyl ester (15 mg, 0.026 mmol) in 10% TFA-CH2Cl2 (1 mL) was stirred at ambient temperature for 10 minutes. The reaction was worked up by removal of the solvent. The residue was dissolved in THF (0.5 mL) and water (0.4 mL) and 1N aqueous NaOH solution (0.1 mL) was added. The solution was stirred at room temperature for 20 minutes when it was acidified with 1N aqueous HCl solution. The resulting solution was purified by RP HPLC using a C18 column with a gradient of H2O, 0.1% TFA-acetonitrile, 0.1% TFA to provide 6.8 mg of the product as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.38 (d, 3H, J=7 Hz), 1.91 (s, 3H), 2.13 (s, 3H), 2.12-2.28 (m, 2H), 3.12-3.33 (m, 2H), 3.41 (d, 2H, J=6 Hz), 3.56 (br s, 2H), 3.75 (s, 3H), 4.71-4.88 (m, 1H), 5.16 (s, 2H), 5.58-5.71 (m, 1H), 7.88 (br s, 3H), 8.60 (br s, 1H), 8.78 (br s, 1H) ppm; 31P (121.4 MHz, CDCl3) δ 22.0 ppm; MS (m/z) 458.3 [M+H]+, 480.3 [M+Na]+.

Aufarbeitung

  1. customThe reaction was worked up by removal of the solvent
  2. dissolutionThe residue was dissolved in THF (0.5 mL)
  3. additionwater (0.4 mL) and 1N aqueous NaOH solution (0.1 mL) was added
  4. customThe resulting solution was purified by RP HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2a6c827e69544dc58d490dfb5b12afb5
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07452901B2

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