(s)-2-Mercaptosuccinic acid → HCID 86632321, Verbindung

HRID 1695951

Reaktionsgleichung

Reaktionsgleichung von HRID 1695951
[F:1][C:2]1[C:3]([N:16]2[CH2:20][CH2:19][CH:18]([F:21])[CH2:17]2)=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH:5]=[N:6][CH2:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10].[SH:22][C@@H:23]([CH2:27][C:28]([OH:30])=[O:29])[C:24](O)=[O:25]>C1(C)C=CC=CC=1>[CH3:10][C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][N:6]1[C:24](=[O:25])[C@@H:23]([CH2:27][C:28]([OH:30])=[O:29])[S:22][CH:5]1[C:4]1[CH:13]=[CH:14][CH:15]=[C:2]([F:1])[C:3]=1[N:16]1[CH2:20][CH2:19][C@H:18]([F:21])[CH2:17]1

Komponenten

4

Edukt 2

HCID 3246154(s)-2-Mercaptosuccinic acidHCID 67276676N-(3-fluoro-2-(3-fluoropyrrolidin-1-yl)benzylidene)-3,3-dimethylbutan-1-amine

Produkt 1

HCID 86632321HCID 86632321, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

N-(3-Fluoro-2-(3-fluoropyrrolidin-1-yl)benzylidene)-3,3-dimethylbutan-1-amine (400 mg, 1.359 mmol) was taken in toluene and (S)-2-mercaptosuccinic acid (204.1 mg, 1.359 mmol) was added. The reaction mixture was refluxed overnight with a Dean Stark trap to remove the water. Then the reaction mixture was concentrated, triturated with ether and dried overnight to give crude 2-((5R)-3-(3,3-dimethylbutyl)-2-(3-fluoro-2-((S)-3-fluoropyrrolidin-1-yl)phenyl)-4-oxothiazolidin-5-yl)acetic acid which was used directly in the next step. The product was identified by HPLC and LC/MS. (LC/MS: m/z=427.2 M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed overnight with a Dean Stark trap
  2. customto remove the water
  3. concentrationThen the reaction mixture was concentrated
  4. customtriturated with ether
  5. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-f0d473d4f6ce460d9a91e98a04d13e6e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163737B2

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