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Cesium carbonate → HCID 69199557, Verbindung

HRID 2376248
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2376248
[CH2:1]([O:3][C:4]([CH:6]([O:8][C:9](=[O:31])[C@H:10]([C:24]1[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=1)[CH2:11][C:12]#[C:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)=O)[CH3:7])=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([NH:47][NH2:48])=[CH:43][CH:42]=1>C1COCC1>[CH2:1]([O:3][C:4]([CH:6]([O:8][C:9](=[O:31])[C@H:10]([C:24]1[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=1)[CH2:11][C:12]1[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[N:47]([C:44]2[CH:45]=[CH:46][C:41]([O:40][CH3:39])=[CH:42][CH:43]=2)[N:48]=1)[CH3:7])=[O:5])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 11583465HCID 11583465, Verbindung

Produkt 1

HCID 69199557HCID 69199557, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-6-(3,4-dichloro-phenyl)-6-oxo-2-m-tolyl-hex-4-ynoic acid 1-ethoxycarbonyl-ethyl ester from Example 502 (15.5 g, 0.0336 mol) in THF (150 mL) was added Cs2CO3 (8.8 g, 0.027 mol) followed by 4-methoxyphenyl hydrazine HCl (6.5 g, 0.037 mol). The resulting slurry was stirred at rt overnight and then slowly quenched with 1 N HCl until pH 2-3. The mixture was transferred to a separatory funnel and extracted with EtOAc (3×75 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to an oil. The crude oil was purified by pad filtration on silica gel using EtOAc/hexanes to obtain the pyrazole as mixture of two regioisomers in 4:1 ratio (18.6 g, 95%). Chiral HPLC (Method S): Rt (R,S)=5.6 min; (S,S)=6.3 min. 1H NMR (400 MHz, CDCl3): 7.31-7.07 (m, 8H), 6.91-6.86 (m, 3H), 6.23 (s, 1H), 5.13 (dd, J=10.4, 7.0 Hz, 1H), 4.16 (m, 1H), 4.07 (dd, J=14.4, 7.2 Hz, 2H), 3.82 (s, 3H), 3.51 (dd, J=14.9, 9.6 1H), 3.04 (dd, J=14.9, 6.3 Hz, 1H), 2.37 (s, 3H), 1.42 (d, J=7.0 Hz, 3H), 1.12 (t, J=7.3 Hz, 3H).

Aufarbeitung

  1. customslowly quenched with 1 N HCl until pH 2-3
  2. customThe mixture was transferred to a separatory funnel
  3. extractionextracted with EtOAc (3×75 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. filtrationThe crude oil was purified by pad filtration on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-bb0576a295e145ef920a4e8dd08d90ad
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07465808B2

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