4-Toluenesulfonyl chloride → HCID 178483172, Verbindung

HRID 1797128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797128
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][N:9]([CH3:20])[C:10](=[O:19])[CH:11](O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[NH2:40][CH2:41][CH2:42][C:43]1[N:47]=[CH:46][NH:45][CH:44]=1>O1CCCC1.CO>[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][N:9]([CH3:20])[C:10](=[O:19])[CH:11]([NH:40][CH2:41][CH2:42][C:43]2[N:47]=[CH:46][NH:45][CH:44]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 22174856N-(2,2-Diphenyl-ethyl)-2-hydroxy-N-methyl-2-phenyl-acetamideHCID 178419017HCID 178419017, Verbindung

Produkt 1

HCID 178483172HCID 178483172, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To stirred solution of the product of step 1 (1.50 g, 4.34 mmol) in tetrahydrofuran (15 mL) was added a 60% dispersion of sodium hydride in mineral oil (0.210 g, 5.25 mmol). After gas evolution ceased, p-toluenesulfonyl chloride (0.990 g, 5.20 mmol) was added and the mixture was stirred for 2 hours. At this time, histamine (1.93 g, 17.4 mmol) was added followed by methanol (10 mL). The reaction was stirred overnight and concentrated. The residue was partitioned between ethyl acetate and aqueous sodium carbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford a pasty white solid. Flash chromatography over silica (methylene chloride/methanolic ammonia solution) provided 1.08 g (57%) of product as a colorless tacky foam: 1H NMR (CDCl3) δ 7.52–7.43 (m, 1H), 7.40–7.00 (m, 15H), 6.78–6.69 (m, 1H), 4.36–3.97 (m, 4H), 2.92–2.20 (m, 7H) ppm.

Aufarbeitung

  1. stirringThe reaction was stirred overnight
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and aqueous sodium carbonate solution
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. concentrationconcentrated
  6. customto afford a pasty white solid

Quellen und Nachweise

ORD-Eintrag
ord-fff33542f648433dbcab01f96252520b
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034031B2

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