Phenol → [(R)-2-(7-nitro-5-phenoxymethyl-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid methyl ester

HRID 1515265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515265
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:10][O:11][C:12](=[O:33])[CH2:13][C@@H:14]1[CH2:18][S:17][C:16]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28]Cl)=[CH:23][C:22]=3[N+:30]([O-:32])=[O:31])=[N:15]1.[NH4+].[Cl-]>CN(C=O)C>[CH3:10][O:11][C:12](=[O:33])[CH2:13][C@@H:14]1[CH2:18][S:17][C:16]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:23][C:22]=3[N+:30]([O-:32])=[O:31])=[N:15]1

Komponenten

6

Edukt 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59543007(R)-2-[(5-chloromethyl-7-nitro-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]acetic acid methylester

Produkt 1

HCID 59543026[(R)-2-(7-nitro-5-phenoxymethyl-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Phenol (192 mg, 2.04 mmol) was dissolved in DMF. NaH (60% mineral oil, 82 mg, 2.04 mmol) was added, and the reaction solution was cooled to 0°. (R)-2-(5-chloromethyl-7-nitro-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl-acetic acid methyl ester (500 mg, 1.36 mmol) prepared in Preparation 42, which was dissolved in DMF, was slowly added thereto. The reaction solution was warmed to room temperature, and stirred for 4 h. After saturated aqueous NH4Cl solution was added to quench the reaction, the reaction mixture was extracted with EtOAc, dried over MgSO4, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (eluent: EtOAc/n-Hex=1/2) to give the title compound.

Aufarbeitung

  1. temperaturethe reaction solution was cooled to 0°
  2. additionwas slowly added
  3. customto quench
  4. customthe reaction
  5. extractionthe reaction mixture was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography (eluent: EtOAc/n-Hex=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-2c0711436e42432293764a1a875129ec
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222414B2

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