Water → Benzyl (S)-2-(6-hydroxy-7-nitro-1H-indazol-1-yl)-1-methylethylcarbamate

HRID 1247007

Reaktionsgleichung

Reaktionsgleichung von HRID 1247007
Br[C:2]1[C:3]([OH:25])=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C@@H:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:13])[N:8]=[CH:7]2.[N+:26]([O-])([O-:28])=[O:27].[Na+].O>O1CCCC1.C(O)(=O)C>[OH:25][C:3]1[C:2]([N+:26]([O-:28])=[O:27])=[C:10]2[C:6]([CH:7]=[N:8][N:9]2[CH2:11][C@@H:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:13])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 24268Sodium NitrateHCID 136207273Benzyl (S)-2-(7-bromo-6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

Produkt 1

HCID 136335131Benzyl (S)-2-(6-hydroxy-7-nitro-1H-indazol-1-yl)-1-methylethylcarbamateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the product from Step B (3.76 g, 9.3 mmol) in tetrahydrofuran (20 mL) and acetic acid (10 mL) was cooled in an ice bath, sodium nitrate (1.93 g, 27.9 mmol) was added and the reaction mixture was stirred for 1 h followed by warming to room temperature and stirring for one hour. Water (150 mL) was added to the reaction mixture, which was extracted with ethyl acetate (2×100 mL). The combined extracts were washed with a saturated aqueous solution of sodium bicarbonate (2×100 m), dried over magnesium sulfate, filtered, and evaporated to an oil (2.87 g). This residue was purified by chromatography (silica gel, hexane/ethyl acetate) to give a tan foam (2.44 g, 71%): LC/MS m/z 371. This was used in the next reaction without further purification.

Aufarbeitung

  1. stirringstirring for one hour
  2. extractionwas extracted with ethyl acetate (2×100 mL)
  3. washThe combined extracts were washed with a saturated aqueous solution of sodium bicarbonate (2×100 m)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil (2.87 g)
  7. customThis residue was purified by chromatography (silica gel, hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0361b1437691424c89c499aa4d7ebca9
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129257B1

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