Tetrahydrofuran → (1S)-1-[5-[4-(2-aminoethoxy)-2-methylbenzyl]-2-(benzyloxy)-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol

HRID 1009876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009876
O1CCCC1.[CH2:6]([O:13][C@@H:14]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:18]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:17]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:16][C@H:15]1[C:45]1[CH:50]=[C:49]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][N:61]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:54][C:53]=2[CH3:72])[C:48]([CH3:73])=[CH:47][C:46]=1[O:74][CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.NN.[OH-].[Na+]>CO>[NH2:61][CH2:60][CH2:59][O:58][C:55]1[CH:56]=[CH:57][C:52]([CH2:51][C:49]2[C:48]([CH3:73])=[CH:47][C:46]([O:74][CH2:75][C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)=[C:45]([C@@H:15]3[O:16][C@H:17]([CH2:36][O:37][CH2:38][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C@@H:18]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C@H:19]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:14]3[O:13][CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:50]=2)=[C:53]([CH3:72])[CH:54]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 86638442HCID 86638442, Verbindung

Produkt 1

HCID 67305276(1S)-1-[5-[4-(2-aminoethoxy)-2-methylbenzyl]-2-(benzyloxy)-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a tetrahydrofuran (0.8 mL) and methanol (0.2 mL) solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)ethoxy]-2-methylbenzyl]-4-methylphenyl]-D-glucitol (60 mg, 0.059 mmol) was added hydrazine monohydrate (30 mg, 0.59 mmol), and the reaction mixture was stirred at 65° C. for an hour. After the mixture was cooled to room temperature, a 2 M aqueous solution of sodium hydroxide was added thereto, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound quantitatively.

Aufarbeitung

  1. temperatureAfter the mixture was cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4a38a38369e8410392990e62fc8375db
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973012B2

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