反応式
O[CH2:2][C:3]1[S:4][S:5][C:6]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:7][CH:8]=1.[Si](OC1[C:27]([OH:36])=[N:28][C:29]2[C:34]([N:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2)(C(C)(C)C)(C)C.[OH:37][C:38]1C(O)=NC2C(=CC=CC=2)N=1.[Si](Cl)(C(C)(C)C)(C)C.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Si:11]([O:10][CH2:9][C:6]1[S:5][S:4][C:3]([C:2]2[C:27]([OH:36])=[N:28][C:29]3[C:34](=[CH:33][CH:32]=[CH:31][C:30]=3[O:37][CH3:38])[N:35]=2)=[CH:8][CH:7]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]参加物
反応物 7
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
To a stirred solution of 3-(hydroxymethyl)-6-[(tert-butyldimethylsilyloxy)methyl]-1,2-dithiin (U.S. Ser. No. 08/212,096) (200 mg, 0.688 mmol) of in 2 mL dry THF was added a solution of 3-(tert-butyldimethylsilyloxy)-2-hydroxyquinoxaline obtained from the reaction of 2,3-dihydroxyquinoxaline with tert-butyldimethylsilyl chloride and imidazole as in Example 6 (248 mg, 1.753 mmol) in 2 mL THF, followed by addition of triphenylphosphine (220 mg, 0.839 mmol). The resulting solution was cooled to 0° C., then 140 μL (155 mg, 0.890 mmol) of diethylazodicarboxylate was added, and the reaction mixture was kept at 0°-5° C. for 2 h until TLC analysis showed the reaction to be complete. For isolation of the products, the reaction mixture poured directly onto a silica gel column and eluted with ethyl acetate-hexane, 1:6, to give 3-[(tert-butyldimethylsilyloxy)methyl]-6-[methyloxy[3-hydroxyquinoxalin-2-yl]]-1,2-dithiin (104 mg, 28.2%). No product of N-alkylation was isolated; MS (+LSIMS) 549.4 (MH+).
後処理
- customthe reaction
- additionFor isolation of the products, the reaction mixture poured directly onto a silica gel column
- washeluted with ethyl acetate-hexane, 1:6
出典と根拠
- ORDレコード
- ord-7f775397e4964fcb85517dbb0ba849bd
- 出典データセット
- uspto-grants-1997_07
- 特許番号
- US05648354
関連ノート
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