Pyridine → (Z)-2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxodihydrofuran-3(2H)-ylidene)methyl)phenyl)acetamide

HRID 1256161노트

반응식

HRID 1256161 반응식
[O:1]=[C:2]1[O:3][CH2:4][CH2:5]/[C:6]/1=[CH:7]/[C:8]1[CH:13]=[C:12]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH:11]=[CH:10][C:9]=1[S:21](Cl)(=[O:23])=[O:22].[NH2:25][C:26]1[CH:27]=[CH:28][C:29]2[CH2:33][O:32][B:31]([OH:34])[C:30]=2[CH:35]=1.N1C=CC=CC=1>O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>[F:17][C:16]([F:19])([F:18])[C:15]([NH:14][C:12]1[CH:11]=[CH:10][C:9]([S:21](=[O:23])(=[O:22])[NH:25][C:26]2[CH:27]=[CH:28][C:29]3[CH2:33][O:32][B:31]([OH:34])[C:30]=3[CH:35]=2)=[C:8](/[CH:7]=[C:6]2\[C:2](=[O:1])[O:3][CH2:4][CH2:5]\2)[CH:13]=1)=[O:20]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655231(Z)-2-((2-oxodihydrofuran-3(2H)-ylidene)methyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride

생성물 1

HCID 86655230(Z)-2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxodihydrofuran-3(2H)-ylidene)methyl)phenyl)acetamide수율 68.5%

시약·촉매·용매 1

HCID 180504Ceric ammonium nitrate용매

실험 절차

The crude intermediate (Z)-2-((2-oxodihydrofuran-3(2H)-ylidene)methyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (2.85 g, 10 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (1.5 g, 10 mmol) was suspended in CAN (50 ml), followed by the addition of pyridine (3 ml) dropwise. After stirred at rt for 3 hrs, the mixture was poured into ice-H2O and extracted with EtOAc, washed with H2O, brine, dried over MgSO4, filtered, concentrated in reduced pressure to dryness. The crude product was treated with DCM to give (Z)-2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxodihydrofuran-3(2H)-ylidene)methyl)phenyl)acetamide as a solid (3.4 g). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.63 (s, 1H), 10.34 (s, 1H), 9.18 (s, 1H), 8.00 (d, J=8.4 Hz, 1H), 7.87 (s, 1H), 7.87 (dd, J=8.4, 1.6 Hz, 1H), 7.82 (t, J=2.8 Hz, 1H), 7.34 (d, J=1.6 Hz, 1H), 7.21 (d, J=8.4 Hz, 1H), 7.07 (dd, J=8.4, 1.6 Hz, 1H), 4.85 (s, 2H), 4.28 (t, J=7.2 Hz, 2H), 2.88 (dt, J=2.8, 7.2 Hz, 2H). MS (ESI) m/z=495 (M−1).

후처리

  1. extractionextracted with EtOAc
  2. washwashed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in reduced pressure to dryness
  6. additionThe crude product was treated with DCM

출처 및 근거

ORD 기록
ord-8cb9e1279734412f98ae6f979793fdfd
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461134B2

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