Ethyl Acetate → HCID 178510469, 화합물

HRID 1873596노트

반응식

HRID 1873596 반응식
[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

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 68699977HCID 68699977, 화합물

생성물 1

HCID 178510469HCID 178510469, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

43 mg (0.06 mmol) of the compound from Example 7A (cis isomer) are dissolved in 5 ml of dry THF, 22 mg (0.08 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 chromatographically initially by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5) and then once more on silica gel 60 (mobile phase: gradient dichloromethane/ethanol 200:1→10:1).

후처리

  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 chromatographically initially by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

출처 및 근거

ORD 기록
ord-b3162cfc6b4e40b1a16e3f26374a1824
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304412B2

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