Triethylamine → 4-{4-[(Tert-butoxycarbonyl)(methyl)amino]butanoyl}benzyl methanesulfonate

HRID 446572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446572
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:22])[CH2:10][CH2:11][CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(=O)([O-])O.[Na+]>ClCCl>[CH3:30][S:31]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:22])[CH2:10][CH2:11][CH2:12][N:13]([C:14]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:20])[CH3:21])=[CH:5][CH:4]=1)(=[O:33])=[O:32]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86663464tert-Butyl {4-[4-(hydroxymethyl)phenyl]-4-oxobutyl}methylcarbamate

Produkt 1

HCID 866634654-{4-[(Tert-butoxycarbonyl)(methyl)amino]butanoyl}benzyl methanesulfonateAusbeute 104,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound (651 mg, 2.12 mmol) obtained in Example 78a was dissolved in dichloromethane (20 mL), triethylamine (0.590 mL, 4.24 mmol) and methanesulfonyl chloride (0.245 mL, 3.18 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 30 minutes. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a crude 4-{4-[(tert-butoxycarbonyl)(methyl)amino]butanoyl}benzyl methanesulfonate (851 mg) as a yellow oily substance.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6f63741b49714124831c69300500b305
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476253B2

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