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

HRID 2103770ノート

反応式

HRID 2103770 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-db9f4483c3c1486ca8f73d316d5a9f05
出典データセット
uspto-grants-2009_08
特許番号
US07576122B2

反応ノート

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