Triethylamine → 3-(3-Tert-butoxycarbonylaminophenyl)propyl methanesulfonate

HRID 1978397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978397
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][OH:18])[CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:19][S:20]([O:18][CH2:17][CH2:16][CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:10]=1)(=[O:22])=[O:21]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21993723tert-butyl N-(3-(3-hydroxypropyl)phenyl)carbamate

Produkt 1

HCID 219939853-(3-Tert-butoxycarbonylaminophenyl)propyl methanesulfonateAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A mixture of 3-(3-tert-butoxycarbonylaminophenyl)propanol (3.24 g, 12.9 mmol), methanesulfonylchloride (1.63 g, 14.2 mmol), triethylamine (1.44 g, 14.2 mmol) and ethyl acetate (50 ml) was stirred at room temperature for 1 hour. Then the reaction mixture was diluted with ethyl acetate and successively washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (50 g) with hexane-ethyl acetate (3:1) to give 3-(3-tert-butoxycarbonylaminophenyl)propyl methanesulfonate as a colorless oil (3.50 g, 82%).

Aufarbeitung

  1. washsuccessively washed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel (50 g) with hexane-ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-5b28f644dd694cb5b0dcde2346ec6832
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235731B1

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