Benzyl mercaptan → 1-{4'-[4-(2-Benzylsulfanyl-1-hydroxy-ethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

HRID 1528919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528919
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]4[CH2:29][O:28]4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:36]([SH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([OH:28])[CH2:29][S:43][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 7509Benzyl mercaptan2×HCID 11430Potassium CarbonateHCID 866524031-[4'-(3-Methyl-4-oxiranyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Produkt 1

HCID 665772271-{4'-[4-(2-Benzylsulfanyl-1-hydroxy-ethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-[4′-(3-Methyl-4-oxiranyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.100 g, 0.26 mmol) and potassium carbonate (0.054 g, 0.39 mmol) were stirred in DMF (5 mL) and then benzyl mercaptan (0.040 mL, 0.31 mmol) was added. After stirring 4 hours at room temperature an additional portion of benzyl mercaptan (0.010 mL) was added. After 1 hour the reaction was submitted to standard aqueous workup and purified on silica gel (0-40% EtOAc in hexanes) to afford the title compound.

Aufarbeitung

  1. additionwas added
  2. custompurified on silica gel (0-40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1470217c9194409cae85877e50bde248
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090573B2

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