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 346969

반응식

HRID 346969 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 fluoride (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 as a white solid. 1H NMR (500 MHz, CD3Cl) δ 1.87–1.64 (m, 21H), 1.70–1.98 (m, 3H), 2.15–2.56 (m, 5H), 2.85–2.94 (m, 1H), 3.71 (d, J=13.91 Hz, 1H), 4.10–4.26 (m, 2H), 4.51 (t, J=7.87 Hz, 1H), 4.62 (s, 1H), 4.98 (m, 1H), 5.06 (d, J=8.78 Hz, 1H), 5.64–5.71 (m, 1H), 6.72 (s, 1H), 10.24 (s, 1H). LC-MS (Method A, retention time: 2.85 min), 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-c0188ebad1194acdafff8f296cefbf12
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173004B2

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