Methanol → (R)-3-(7-chloro-4-(hydroxymethyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

HRID 132443

Reaktionsgleichung

Reaktionsgleichung von HRID 132443
[C:1]([O:9][C@H:10]([CH2:15][C:16]1[C:17]([CH2:26][O:27]C(=O)C)=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[NH:21][N:20]=[CH:19]2)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.CO.C[O-].[Mg+2].C[O-]>>[C:1]([O:9][C@H:10]([CH2:15][C:16]1[C:17]([CH2:26][OH:27])=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[NH:21][N:20]=[CH:19]2)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 4

HCID 887MethanolHCID 6212ChloroformHCID 164537Methanol, magnesium salt (2:1)HCID 59732064(R)-3-(4-(acetoxymethyl)-7-chloro-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

Produkt 1

HCID 59732062(R)-3-(7-chloro-4-(hydroxymethyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoateAusbeute 67 %

Versuchsvorschrift

(R)-3-(4-(acetoxymethyl)-7-chloro-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate (8.5g, 19.73 mmol) in a mixture of chloroform (80.0 ml, 992 mmol) and methanol (60.0 ml, 1483 mmol) was added magnesium methoxide (4.18 ml, 39.5 mmol). After 3 h, quenched with 1.0 M HCl and extracted with dichloromethane (300 mL). The crude product was purified by flash chromatography using 70% EtOAc in hexane to give (R)-3-(7-chloro-4-(hydroxymethyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate in 67% yield. 1H NMR (500 MHz, CDCl3): in δ 8.09 (s, 1H), 7.93 (d, J=7.5 Hz, 1H), 7.47 (m, 1H), 7.32 (t, J=8 Hz, 2H), 7.22 (s, 1H), 5.49 (m, 1H), 4.99 (m, 2H), 3.45-3.41 (m, 1H), 3.68 (s, 3H), 3.36-3.31 (m, 1H); MS (ESI) 389 (M+H); Rf=2.07.

Aufarbeitung

  1. customquenched with 1.0 M HCl
  2. extractionextracted with dichloromethane (300 mL)
  3. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cd3f5188bd7d4314b3f438c5af0538c8
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384931B2

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