Ethyl bromoacetate → HCID 68857640, Verbindung

HRID 1453891

Reaktionsgleichung

Reaktionsgleichung von HRID 1453891
[CH2:1]([O:8][C:9](=[O:26])[NH:10][C@@H:11]([CH3:25])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[C:20]=2[CH:22]=O)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[CH2:38]([O:37][C:35]([C:34]1[O:24][C:19]2=[CH:18][CH:17]=[C:16]3[C:21]([N:13]([CH2:12][C@@H:11]([NH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:26])[CH3:25])[N:14]=[CH:15]3)=[C:20]2[CH:22]=1)=[O:36])[CH3:39]

Komponenten

7

Edukt 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 136385114Benzyl [(1S)-2-(7-formyl-6-hydroxy-1H-indazol-1-yl)-1-methylethyl]carbamate

Produkt 1

HCID 68857640HCID 68857640, VerbindungAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of the product from Step C (0.20 g, 0.56 mmol) in DMF (10 mL) was added potassium carbonate (0.23 g, 1.68 mmol) followed by ethyl 2-bromoacetate (0.07 mL, 0.62 mmol) at room temperature and the resultant solution was heated at 70° C. for 20 h. Saturated aqueous ammonium chloride (20 mL) was added followed by ethyl acetate (50 mL). The organic layer was separated and the aqueous was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (30 mL), dried and evaporated. The residue was purified by chromatography (silica, 50% ethyl acetate in hexane) to give an oil (0.10 g, 42%): MS(ES) m/z 422 (M+); 1H NMR (CDCl3) δ 8.17 (s, 1H), 8.05 (s, 1H), 7.72 (d, 1H, J=8.8 Hz), 7.43 (d, 1H, J=8.8 Hz), 7.33 (m, 5H), 5.05-5.09 (m, 2H), 4.58 (m, 1H), 4.30 (m, 2H), 1.45 (t, 3H, J=7.2 Hz), 1.17 (d, 3H, J=6.8 Hz).

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography (silica, 50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2feda30b31494016b4fe93da723e659e
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476687B2

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