Ethyl Acetate → HCID 178510470、化合物

HRID 1873595ノート

反応式

HRID 1873595 の反応式
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH:13]([O:16][CH2:17][CH2:18][O:19][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:12][CH2:11]2)[C:5]([C:37]#[N:38])=[C:4]([S:39][CH2:40][C:41]2[N:42]=[C:43]([C:46]3[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=3)[S:44][CH:45]=2)[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C@H:10]2[CH2:15][CH2:14][C@H:13]([O:16][CH2:17][CH2:18][OH:19])[CH2:12][CH2:11]2)[C:5]([C:37]#[N:38])=[C:4]([S:39][CH2:40][C:41]2[N:42]=[C:43]([C:46]3[CH:47]=[CH:48][C:49]([Cl:52])=[CH:50][CH:51]=3)[S:44][CH:45]=2)[N:3]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 68699977HCID 68699977、化合物

生成物 1

HCID 178510470HCID 178510470、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

35 mg (0.05 mmol) of the compound from Example 7A (trans isomer) are dissolved in 5 ml of dry THF, 18 mg (0.07 mmol) of tetra-n-butylammonium fluoride are added and the mixture is stirred at RT for 20 h. 15 ml of ethyl acetate are then added to the mixture. The mixture is washed twice with in each case 3 ml of saturated aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate. After removal of the solvent on a rotary evaporator the crude product is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

後処理

  1. washThe mixture is washed twice with in each case 3 ml of saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customAfter removal of the solvent
  4. customon a rotary evaporator the crude product
  5. customis purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

出典と根拠

ORDレコード
ord-d1ecbfceca0f443c92474e9e3e428962
出典データセット
uspto-grants-2012_11
特許番号
US08304412B2

反応ノート

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