4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-[tert-butoxycarbonyl-(3-fluoro-benzyl)-amino]-ethyl ester

HRID 8639

Reaktionsgleichung

Reaktionsgleichung von HRID 8639
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][C:13]([O:16][C:17](=[O:30])[N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[CH2:19][CH2:20][OH:21])([CH3:15])[CH3:14].FC1C=C(C=CC=1)CNCCO.C(N(CC)CC)C>ClCCl>[C:13]([O:16][C:17]([N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[CH2:19][CH2:20][O:21][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])=[O:30])([CH3:12])([CH3:14])[CH3:15]

Komponenten

6

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 108667492-(3-Fluoro-benzylamino)-ethanolHCID 69653122tert-butyl N-[(3-fluorophenyl)methyl]-N-(2-hydroxyethyl)carbamate

Produkt 1

HCID 23548235Toluene-4-sulfonic acid 2-[tert-butoxycarbonyl-(3-fluoro-benzyl)-amino]-ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add p-toluenesulfonyl-chloride (0.71 g, 3.71 mmol), portionwise, to a mixture of (3-fluoro-benzyl)-(2-hydroxy-ethyl)-carbamic acid dimethyl-ethyl ester (1 g, 3.71 mmol, prepared from 2-(3-fluoro-benzylamino)-ethanol by methods as are known in the art), triethylamine (0.751 g, 7.4 mmol) and dichloromethane (6 mL). Stir the resulting suspension vigorously overnight at room temperature. Add water (10 mL), separate the organic layer, and extract the aqueous layer with dichloromethane (5 mL), twice. Combine the organic layers and wash with citric acid (5 mL, 20% in water), dry with sodium sulfate and evaporate the solvent to give the final, desired compound. The final compound may be purified by chromatography.

Aufarbeitung

  1. customAdd water (10 mL), separate the organic layer
  2. extractionextract the aqueous layer with dichloromethane (5 mL)
  3. washwash with citric acid (5 mL, 20% in water)
  4. dry with materialdry with sodium sulfate
  5. customevaporate the solvent

Quellen und Nachweise

ORD-Eintrag
ord-3bfb9478b47f4e919a8a0e2f00a8190d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091199B1

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