Water → HCID 59619202, Verbindung

HRID 1367552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367552
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@H:10]2[CH2:25][O:26]CC2C=CC(OC)=CC=2)=[O:8])[CH2:5][CH2:4]1)#[N:2].O>ClCCl>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:15])=[O:16])[CH2:11][C@H:10]2[CH2:25][OH:26])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Komponenten

4

Edukt 2

HCID 962WaterHCID 59619362HCID 59619362, Verbindung

Produkt 1

HCID 59619202HCID 59619202, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cold mixture of (1R,2R,4S)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(4-methoxy-benzyloxymethyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (example 153, step 9, 171 mg) in dichloromethane (4 mL) was added water (0.2 mL) and dichlorodicyanoquinone (97 mg). The reaction mixture was stirred 90 min at room temperature. The suspension was filtered and the solid was washed with dichloromethane. The resulting liquor was partionned between dichloromethane and saturated aqueous solution of sodium hydrogenocarbonate. The aqueous layer was washed with dichloromethane. The combined organic layers were washed brine, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of dichlormethane:methanol (98:2 to 19:1 v/v) as eluant to afford the title compound (101 mg, 77%) as a white solid. MS (EI): 401.1 (M+H)+.

Aufarbeitung

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with dichloromethane
  3. washThe aqueous layer was washed with dichloromethane
  4. washThe combined organic layers were washed brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel with a gradient of dichlormethane:methanol (98:2 to 19:1 v/v) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-1b258d13f53a49a79c6550722476dabb
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893099B2

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