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Methanol → (2R,4S)-5-biphenyl-4-yl-4-((2S,3S)-2,3-diacetoxy-3-carboxy-propionylamino)-2-methyl-pentanoic acid

HRID 1469602
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1469602
Cl.C([O:9][C:10](=[O:29])[C@H:11]([CH3:28])[CH2:12][C@H:13]([NH2:27])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)C1C=CC=CC=1.[C:30]([O:33][C@@H:34]1[C:38](=[O:39])[O:37][C:36](=[O:40])[C@H:35]1[O:41][C:42](=[O:44])[CH3:43])(=[O:32])[CH3:31].C(Cl)Cl.N1C=CC=CC=1.CO>C(OCC)(=O)C.[Pd]>[C:18]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:17]=[CH:16][C:15]([CH2:14][C@@H:13]([NH:27][C:38](=[O:39])[C@@H:34]([O:33][C:30](=[O:32])[CH3:31])[C@H:35]([O:41][C:42](=[O:44])[CH3:43])[C:36]([OH:37])=[O:40])[CH2:12][C@@H:11]([CH3:28])[C:10]([OH:29])=[O:9])=[CH:20][CH:19]=1
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Komponenten

7

Edukt 4

HCID 887MethanolHCID 12731855Diacetyltartaric anhydride, D-HCID 21875418Pyridine methylene chlorideHCID 67505899HCID 67505899, Verbindung

Produkt 1

HCID 49821388(2R,4S)-5-biphenyl-4-yl-4-((2S,3S)-2,3-diacetoxy-3-carboxy-propionylamino)-2-methyl-pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (2R,4S)-4-amino-5-biphenyl-4-yl-2-methyl-pentanoic acid benzyl ester hydrochloride (100 mg, 0.287 mmol) and acetic acid (3S,4S)-4-acetoxy-2,5-dioxo-tetrahydro-furan-3-yl ester (0.431 mmol) in 1:1 methylene chloride/pyridine (1.4 mL) is stirred at room temperature for 24 hours. The solvents are removed under reduced pressure and obtained residue is used directly in the subsequent hydrolysis reaction. Next, a solution of the benzyl ester in ethyl acetate is hydrogenated at 1 atm over 10% Pd/C for 18 hours. Methanol is added and the catalyst is filtered through Celite. The Solvent is removed under reduced pressure and the residue is purified by preparative HPLC using a gradient of 10-100% MeCN/water (0.1% TFA). The proper fractions are lyophilized to furnish (2R,4S)-5-biphenyl-4-yl-4-((2S,3S)-2,3-diacetoxy-3-carboxy-propionylamino)-2-methyl-pentanoic acid. HPLC Retention time 0.95 minutes (condition A); MS 500.3 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (d, J=7.20Hz, 3H), 1.45 (m, 1H), 1.82 (m, 1H), 2.39 (m, 1H), 2.70 (d, J=6.82Hz, 2H), 4.01 (m, 1H), 5.38 (m, 2H), 7.19 (d, J=8.21Hz, 2H), 7.34 (t, 1H), 7.45 (t, 2H), 7.53 (d, J=8.21Hz, 2H), 7.64 (d, J=7.20Hz, 2H), 8.00 (d, J=8.72Hz, 1H).

Aufarbeitung

  1. customThe solvents are removed under reduced pressure
  2. customobtained residue
  3. customis used directly in the subsequent hydrolysis reaction
  4. filtrationthe catalyst is filtered through Celite
  5. customThe Solvent is removed under reduced pressure
  6. customthe residue is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-560d5e9d6d9a49c6abcd79be3156b768
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09006249B2

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