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Triethylamine → methyl N-t-butoxycarbonyl-S-[(3,4-methylenedioxy)phenyl]cysteinate

HRID 483804
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 483804
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([SH:10])=[CH:4][C:3]=2[O:2]1.[C:11]([O:15][C:16]([NH:18][C@H:19]([C:32]([O:34][CH3:35])=[O:33])[CH2:20]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:11]([O:15][C:16]([NH:18][C@H:19]([C:32]([O:34][CH3:35])=[O:33])[CH2:20][S:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27598473,4-(Methylenedioxy)thiophenolHCID 7009424Boc-Ser(Tos)-OMe

Produkt 1

HCID 18652697methyl N-t-butoxycarbonyl-S-[(3,4-methylenedioxy)phenyl]cysteinateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

After 27.7 g of (3,4-methylenedioxy)thiophenol and 74 g of methyl N-(t-butoxycarbonyl)-O-tosyl-L-serinate were dissolved in 200 ml of chloroform, 20 g of triethylamine were added at room temperature, followed by stirring overnight. The reaction mixture was washed with water and then extracted with ethyl acetate. The extract so obtained was dried over anhydrous magnesium sulfate. After the solvent was distilled off, 49 g of crude oil were obtained. The crude oil was recrystallized from an ethyl acetatehexane system, whereby 42 g of methyl N-t-butoxycarbonyl-S-[(3,4-methylenedioxy)phenyl]cysteinate were obtained (yield: 66%).

Aufarbeitung

  1. washThe reaction mixture was washed with water
  2. extractionextracted with ethyl acetate
  3. extractionThe extract so
  4. customobtained
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. custom49 g of crude oil were obtained
  8. customThe crude oil was recrystallized from an ethyl acetatehexane system

Quellen und Nachweise

ORD-Eintrag
ord-b7ea69842239425ca8143b0c5d4aa26f
Quelldatensatz
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05227398

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