ethyl[(1R)-9-[(1S)-1-(4-chlorophenyl)ethyl]-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate → 2-((R)-9-((S)-1-(4-chlorophenyl)ethyl)-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl)acetic acid

HRID 1744881

Reaktionsgleichung

Reaktionsgleichung von HRID 1744881
C(C(C1C2NC3C(=CC(F)=CC=3S(C)(=O)=O)C=2CCC1)C([O-])=O)C.C([O:27][C:28](=[O:57])[CH2:29][C@@H:30]1[C:42]2[N:41]([C@H:43]([C:45]3[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=3)[CH3:44])[C:40]3[C:35](=[CH:36][C:37]([F:56])=[CH:38][C:39]=3[S:52]([CH3:55])(=[O:54])=[O:53])[C:34]=2[CH2:33][CH2:32][CH2:31]1)C.C(OC(=O)C[C@H]1C2N([C@H](C3C=CC(Cl)=CC=3)C)C3C(=CC(F)=CC=3S(C)(=O)=O)C=2CCC1)C>>[Cl:51][C:48]1[CH:47]=[CH:46][C:45]([C@@H:43]([N:41]2[C:42]3[C@@H:30]([CH2:29][C:28]([OH:57])=[O:27])[CH2:31][CH2:32][CH2:33][C:34]=3[C:35]3[C:40]2=[C:39]([S:52]([CH3:55])(=[O:53])=[O:54])[CH:38]=[C:37]([F:56])[CH:36]=3)[CH3:44])=[CH:50][CH:49]=1

Komponenten

4

Edukt 3

HCID 66967751ethyl[(1R)-9-[(1S)-1-(4-chlorophenyl)ethyl]-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetateHCID 86594996(+/-) ethyl[6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetateHCID 86615644ethyl[(1S)-9-[(1S)-1-(4-chlorophenyl)ethyl]-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate

Produkt 1

HCID 112597972-((R)-9-((S)-1-(4-chlorophenyl)ethyl)-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl)acetic acid

Versuchsvorschrift

Alternatively (+/−) ethyl[6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate was used for the alkylation reaction in step 5 to give a mixture of 2 diastereomers: ethyl[(1R)-9-[(1S)-1-(4-chlorophenyl)ethyl]-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate and ethyl[(1S)-9-[(1S)-1-(4-chlorophenyl)ethyl]-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate. The diastereomeric mixture was resolved by selective hydrolysis using the following procedure to give the desired [(1R)-9-[(1S)-1-(4-chlorophenyl)ethyl]-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetic acid.

Aufarbeitung

  1. customto give
  2. additiona mixture of 2 diastereomers
  3. customThe diastereomeric mixture was resolved by selective hydrolysis

Quellen und Nachweise

ORD-Eintrag
ord-55571b340d1d475ea6b7fb85caf35347
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07019022B2

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