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Benzyl Bromide → (RS,SR)-2-benzenesulfonyl-N-benzyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide

HRID 602765
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 602765
C(OC([N:8]1[C:20]2[CH2:19][CH:18]([C:21]([S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])([F:26])[C:22](=[O:25])[NH:23][CH3:24])[CH2:17][CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([Cl:36])[CH:13]=2)=O)(C)(C)C.[H-].[Na+].Br[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1>[C:30]1([S:27]([C:21]([CH:18]2[CH2:17][CH2:16][C:15]3[C:14]4[C:9](=[CH:10][CH:11]=[C:12]([Cl:36])[CH:13]=4)[NH:8][C:20]=3[CH2:19]2)([F:26])[C:22]([N:23]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH3:24])=[O:25])(=[O:28])=[O:29])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
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Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 67267476(RS,SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester

Produkt 1

HCID 11237793(RS,SR)-2-benzenesulfonyl-N-benzyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

60 mg (0.112 mmol) of (RS,SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester (from example 59.1) in 3 mL of THF were treated with 7 mg (0.168 mmol, 1.5 eq) of NaH (55% in oil) at 0° C. over 40 min. 38 mg (0.224 mmol, 2eq) of bromomethly-benzene were added and the reaction mixture was stirred over night at RT. The solvent was evaporated, the residue was dissolved in 3 mL of CH2Cl2, 1 mL of TFA was added, and the reaction mixture was stirred over night at RT. Evaporation of the solvent and purification of the residue by preparative HPLC (C18 column) yielded 35 mg (60%) of (RS,SR)-2-benzenesulfonyl-N-benzyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide as a white solid, MS: 525 (MH+).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 3 mL of CH2Cl2
  3. addition1 mL of TFA was added
  4. stirringthe reaction mixture was stirred over night at RT
  5. customEvaporation of the solvent and purification of the residue by preparative HPLC (C18 column)

Quellen und Nachweise

ORD-Eintrag
ord-ded6d0c159274c3db0dffdc2ba0e8dae
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07906546B2

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