1,2-Dichloroethane → 1-tert-butyl-6-methoxy-3H-pyrano[3,4-b][1]benzofuran-3-one

HRID 2103770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2103770
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([C:5]1[O:6][C:7]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:8]=2[C:9]=1[CH2:10][C:11]([OH:13])=[O:12])=O.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:2]([C:3]1[O:12][C:11](=[O:13])[CH:10]=[C:9]2[C:8]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:7]=3[O:6][C:5]=12)([CH3:21])([CH3:20])[CH3:1]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57804476[2-(2,2-Dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]acetic acid

Produkt 1

HCID 578044781-tert-butyl-6-methoxy-3H-pyrano[3,4-b][1]benzofuran-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dissolve 98 mg [2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]acetic acid from the Step B Example 1, 176 μL DIEA, and 114 mg HOBt in 3.5 mL dry DMF. Add 97.1 mg EDC and let the mixture stir at room temperature over night. It was purified directly on RP-HPLC using 50-70% MeCN gradient. The fractions containing pure product were pooled and lyophilized to give the title compound as yellow solid. 1H NMR (CDCl3, 500 MHz) 7.34 (dd, J=1.3 & 8.4 Hz, 1H), 7.25˜7.29 (m, 2H), 6.54 (s, 1H), 3.92 (s, 3H), 1.52 (s, 9H). LC-MS: 3.55 min. (M+H=273.1).

Aufarbeitung

  1. customIt was purified directly on RP-HPLC using 50-70% MeCN gradient
  2. additionThe fractions containing pure product

Quellen und Nachweise

ORD-Eintrag
ord-db9f4483c3c1486ca8f73d316d5a9f05
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576122B2

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