Tetrabutylammonium Fluoride → tert-butyl N-[4-(cyclopropylsulfonylcarbamoyl)-18-hydroxy-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-en-14-yl]carbamate

HRID 500372

반응식

HRID 500372 반응식
[C:1]([O:5][C:6](=[O:46])[NH:7][CH:8]1[C:26](=[O:27])[N:25]2[CH:21]([CH2:22][CH:23]([O:28][Si](C(C)(C)C)(C)C)[CH2:24]2)[C:20](=[O:36])[NH:19][C:18]2([C:37]([NH:39][S:40]([CH:43]3[CH2:45][CH2:44]3)(=[O:42])=[O:41])=[O:38])[CH:16]([CH2:17]2)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6](=[O:46])[NH:7][CH:8]1[C:26](=[O:27])[N:25]2[CH:21]([CH2:22][CH:23]([OH:28])[CH2:24]2)[C:20](=[O:36])[NH:19][C:18]2([C:37]([NH:39][S:40]([CH:43]3[CH2:45][CH2:44]3)(=[O:41])=[O:42])=[O:38])[CH:16]([CH2:17]2)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 66915233[18-(Tert-butyl-dimethyl-silanyloxy)-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 68797769tert-butyl N-[4-(cyclopropylsulfonylcarbamoyl)-18-hydroxy-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-en-14-yl]carbamate수율 73%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of [18-(tert-butyl-dimethylsilanyloxy)-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester (330 mg, 0.48 mmoL) in 25 mL of THF was added tetrabutylammonium floride (150 mg, 0.54 mmoL). The reaction mixture was stirred at rt for 18 h, and then the THF was removed by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and concentrated in vacuo to give the crude product. It was then purified by triturating with hexane to yield 200 mg (73%) of (4-cyclopropanesulfonylaminocarbonyl-18-hydroxy-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl)-carbamic acid tert-butyl ester, Example 19, as a white solid. 1H NMR (500 MHz, CD3Cl) δ 1.87-1.64 (m, 21H), 1.70-1.98 (m, 3 H), 2.15-2.56 (m, 5H), 2.85-2.94 (m, 1H), 3.71 (d, J=13.91Hz, 1H), 4.10-4.26 (m, 2H), 4.51 (t, J=7.87Hz, 1H), 4.62 (s, 1H), 4.98 (m, 1H), 5.06 (d, J=8.78Hz, 1H), 5.64-5.71 (m, 1H), 6.72 (s, 1H), 10.24 (s, 1H); MS m/z 569 (M++1).

후처리

  1. customthe THF was removed by rotary evaporation
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customIt was then purified
  7. customby triturating with hexane

출처 및 근거

ORD 기록
ord-9f38f8b73e584579b003f2de1ddbd8a0
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772183B2

연결된 노트

불러오는 중…