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Triethylamine → 1-methanesulphonyloxy-3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butane

HRID 1533068
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1533068
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[C:19]([C:21]2[C:22]3[CH2:23][CH2:24][CH2:25][CH2:26][C:27]=3[CH:28]=[CH:29][CH:30]=2)=[O:20])[CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[CH3:38][S:39]([O:12][CH2:11][CH2:10][C@@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]([C:21]1[C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][C:27]=2[CH:28]=[CH:29][CH:30]=1)=[O:20])(=[O:41])=[O:40]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 540642943(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butan-1-ol

Produkt 1

HCID 598865681-methanesulphonyloxy-3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butaneAusbeute 102,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

3(S)-(3,4-Dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butan-1-ol (0.68 g) (see Preparation 103) and triethylamine (0.22 g) were dissolved in dichloromethane (15 ml), the solution cooled in an ice-bath and methanesulphonyl chloride (0.22 g) added. The mixture was stirred for 4 hours before removal of the solvent under reduced pressure to give a residue which was partitioned between ethyl acetate and water. The organic phase was separated and washed with saturated aqueous sodium hydrogen carbonate solution before being dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure to give 1-methanesulphonyloxy-3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butane (0.82 g) as an oil.

Aufarbeitung

  1. temperaturethe solution cooled in an ice-bath
  2. customto give a residue which
  3. customwas partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialbefore being dried over anhydrous sodium sulphate
  7. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4673066cc35d4a32b5fe95ffa8d1bc81
Quelldatensatz
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06207678B1

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