Methanesulfonyl chloride → Tert-butyl 1-(4-chlorophenyl)-2-(methylsulfonamido)ethylcarbamate

HRID 423088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423088
[NH2:1][CH2:2][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.C(N(C(C)C)C(C)C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C1COCC1>[Cl:10][C:7]1[CH:6]=[CH:5][C:4]([CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:2][NH:1][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57750386tert-butyl N-[2-amino-1-(4-chlorophenyl)ethyl]carbamate2×

Produkt 1

HCID 57750380Tert-butyl 1-(4-chlorophenyl)-2-(methylsulfonamido)ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 2-amino-1-(4-chlorophenyl)ethylcarbamate (Intermediate 73) (220 mg, 0.81 mmol) and N-ethyldiisopropylamine (0.281 mL, 1.63 mmol) in THF (5 mL) was treated with methanesulfonyl chloride (0.075 mL, 0.98 mmol). The resulting solution was stirred at ambient temperature for 2 hours. The mixture was partitioned between DCM and sodium bicarbonate solution. The organic layer was concentrated and the residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 30% ethyl acetate/DCM). The desired product, tert-butyl 1-(4-chlorophenyl)-2-(methylsulfonamido)ethylcarbamate, was thus isolated as a colourless solid (154 mg, 54.3%).

Aufarbeitung

  1. customThe mixture was partitioned between DCM and sodium bicarbonate solution
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 30% ethyl acetate/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-3308806f7f1c40d19db2c5a3af54acf2
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101623B2

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