Triphenylphosphine → HCID 178499263, Verbindung

HRID 73179

Reaktionsgleichung

Reaktionsgleichung von HRID 73179
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClN1C(=O)CCC1=O.[CH3:38][O:39][C:40]([C:42]1[S:43][C:44]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[CH:45][C:46]=1[NH:47][CH:48]1[CH2:57][CH2:56][C:51]2([O:55][CH2:54][CH2:53][O:52]2)[CH2:50][CH2:49]1)=[O:41].C([O-])(O)=O.[Na+]>ClCCCl.C(OCC)(=O)C>[CH3:38][O:39][C:40]([C:42]1[S:43][C:44]([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)=[CH:45][C:46]=1[N:47]([CH:48]1[CH2:49][CH2:50][C:51]2([O:55][CH2:54][CH2:53][O:52]2)[CH2:56][CH2:57]1)[C:8]([C@H:5]1[CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:7][CH2:6]1)=[O:10])=[O:41]

Komponenten

8

Edukt 5

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 597522913-(1,4-Dioxa-spiro[4.5]dec-8-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl esterHCID 178461286HCID 178461286, Verbindung

Produkt 1

HCID 178499263HCID 178499263, VerbindungAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To trans 4-methyl-cyclohexanecarboxylic acid (148 mg, 1.044 mmol) and triphenylphosphine (274 mg, 1.044 mmol) dissolved in 1,2-dichloroethane (1.5 ml) was added N-chlorosuccinimide (145 mg, 1.084 mmol). After 15 minutes of stirring at room temperature, a solution of 3-(1,4-Dioxa-spiro[4.5]dec-8-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (300 mg, 0.803 mmol) in 1,2-dichloroethane (1.5 ml) was added. The resulting mixture was then stirred for 18 h at 90° C. and then cooled to room temperature. It was then diluted with ethyl acetate (10 ml) and a solution of saturated NaHCO3 (10 ml) was added. The aqueous phase was separated and washed with ethyl acetate (2×10 ml) and the combined organic layers were dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0% to 30% EtOAc/Hexane) to obtain 265 mg (66%) of 3-[(1,4-Dioxa-spiro[4.5]dec-8-yl)-(trans 4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester.

Aufarbeitung

  1. stirringThe resulting mixture was then stirred for 18 h at 90° C.
  2. temperaturecooled to room temperature
  3. customThe aqueous phase was separated
  4. washwashed with ethyl acetate (2×10 ml)
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (0% to 30% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bcb536c805c8478baf7f85a12c57fdb6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829030B2

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