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Hydrochloric Acid → HCID 178527405, Verbindung

HRID 853138
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 853138
[CH2:1]([S:8]([N:11]([CH2:35][C:36]([F:39])([F:38])[F:37])[C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:27][Si](CC)(CC)CC)([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])[CH2:14][CH2:13]1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:50](Br)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.Cl>C1COCC1.CCOCC>[F:39][C:36]([F:37])([F:38])[CH2:35][N:11]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([OH:27])([C:19]([F:22])([F:20])[F:21])[C:23]([F:24])([F:25])[F:26])[CH2:14][CH2:13]1)[S:8]([CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=[O:10])=[O:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 2733832Lithium hexamethyldisilazaneHCID 178477575HCID 178477575, Verbindung

Produkt 1

HCID 178527405HCID 178527405, VerbindungAusbeute 105,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 50 mg (0.08 mmol) of trans benzyl-N-(2,2,2-trifluoro-ethyl)-N-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-sulfonamide (example 30.1) in 0.5 mL of THF was cooled to −78° C. and treated with 0.11 mL of a 1M solution lithium bis(trimethylsilyl)amide in THF. The mixture was allowed to reach ca −5° C. within 30 min and treated with 0.11 mL (0.1 mmol) of benzylbromide. The mixture was stirred overnight and distributed between diluted aqueous solution of HCl and Et2O. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The residue was redissolved in MeOH and treated with 0.5 mL of a 2M solution of NaOMe in MeOH. Distribution of this solution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4, evaporation and column chromatography on silica gel with heptane/EtOAc 4:1 gave 50 mg (76%) of (rac) trans 1,2-diphenyl-ethanesulfonic acid (2,2,2-trifluoro-ethyl)-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide as a colorless foam, MS: 590 (M−H)−.

Aufarbeitung

  1. dry with materialThe combined organic phases were dried over Na2SO4
  2. customthe solvent was evaporated
  3. dissolutionThe residue was redissolved in MeOH
  4. additiontreated with 0.5 mL of a 2M solution of NaOMe in MeOH
  5. dry with materialDistribution of this solution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4, evaporation and column chromatography on silica gel with heptane/EtOAc 4:1

Quellen und Nachweise

ORD-Eintrag
ord-5fa07ce44b4843009a2109e121738289
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07253282B2

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