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2-Aminothiophenol → 3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-

HRID 1457250
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1457250
COC1C=CC([C@@H]2O[C@H]2C(N)=O)=CC=1.NC1C=CC=CC=1S.N[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30][CH:31]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[CH:32]([OH:36])[C:33]([NH2:35])=[O:34].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.ClC1C=CC=CC=1>[OH:36][C@H:32]1[C:33](=[O:34])[NH:35][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30][C@H:31]1[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1
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Komponenten

7

Edukt 4

HCID 87132-AminothiophenolHCID 521998p-Toluenesulfonic acid monohydrateHCID 10821599(2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionamideHCID 538426453-(2-Aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide

Produkt 1

HCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-Ausbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

A mixture of (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionamide (3.86 g) and chlorobenzene (77 ml) is refluxed with heating under nitrogen atmosphere. When the reflux is started, a solution of 2-aminothiophenol (2.75 g) and ferric chloride hexahydrate (0.54 mg) in methanol (0.1 ml) is added immediately into the reaction mixture, and the mixture is reacted at the same temperature for 5 minutes. The reaction mixture is subjected to HPLC analysis* to confirm the production of 3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide (6.09 g) [(2S,3S)/(2S,3R)=91.5/8.5]. To the reaction mixture is added p-toluenesulfonic acid monohydrate (0.76 g), and the mixture is refluxed for 32 hours, and concentrated under reduced pressure to remove the chlorobenzene. To the residue is added methanol (25 ml), and the mixture is refluxed for one hour, and cooled with ice overnight. The precipitated crystals are collected by filtration, washed with methanol, and dried at 50° C. to give (2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (4.76 g).

Aufarbeitung

  1. temperatureis refluxed
  2. temperaturewith heating under nitrogen atmosphere
  3. customthe mixture is reacted at the same temperature for 5 minutes
  4. temperaturethe mixture is refluxed for 32 hours
  5. concentrationconcentrated under reduced pressure
  6. customto remove the chlorobenzene
  7. additionTo the residue is added methanol (25 ml)
  8. temperaturethe mixture is refluxed for one hour
  9. temperaturecooled with ice overnight
  10. filtrationThe precipitated crystals are collected by filtration
  11. washwashed with methanol
  12. customdried at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-b5c08fa0d8e84286b9c2482b456ce7f0
Quelldatensatz
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05847122

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