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4-Toluenesulfonyl chloride → N-tert-Butoxycarbonyl-cis-4-(p-Toluenesulfonyloxy)-D-Proline Methyl Ester

HRID 2185415
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2185415
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14](=[O:28])[C@H:15]1[CH2:19][C@@H:18]([OH:20])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:12][O:13][C:14](=[O:28])[C@H:15]1[CH2:19][C@@H:18]([O:20][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22]
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Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 6951202(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Produkt 1

HCID 13425770N-tert-Butoxycarbonyl-cis-4-(p-Toluenesulfonyloxy)-D-Proline Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

4-Dimethylaminopyridine (1.21 g) and p-toluenesulfonyl chloride (1.51 g) were added to a solution of N-tert-butoxycarbonyl-cis-4-hydroxy-D-proline methyl ester (A, 971 mg) in dichloromethane (20 mL). After stirrng at room temperature for 4 hr, the solvent was removed in vacuo. The residue was diluted with ethyl acetate, and washed with 10% citric acid, water, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform then chloroform:ethyl acetate=1:50, v/v) to give the title compound (1.65 g) as a colorless oil.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 10% citric acid, water, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform

Quellen und Nachweise

ORD-Eintrag
ord-69920ede65644d28adbf8517628fbcb8
Quelldatensatz
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06399629B1

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