Water → HCID 178461142, 화합물

HRID 1036538노트

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HRID 1036538 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[C@H:30]1[CH2:35][CH2:34][C@@H:33]([C:36]([F:39])([F:38])[CH3:37])[CH2:32][CH2:31]1)(=O)=O.O>CC(O)(C)C.CC(=O)CC>[F:38][C:36]([C@H:33]1[CH2:34][CH2:35][C@H:30]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C@:12]2([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]2)[CH:6]=[CH:5]3)[CH2:31][CH2:32]1)([F:39])[CH3:37]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneHCID 178461150HCID 178461150, 화합물

생성물 1

HCID 178461142HCID 178461142, 화합물수율 104.3%

시약·촉매·용매 1

HCID 86642925t-Butanol 2-butanone용매

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온도
110 °C

실험 절차

(R)-4-(6-Hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (121 mg, 0.5 mmol, 0.9 eq.) and cesium carbonate (407 mg, 1.25 mmol, 2.5 eq.) were dissolved in t-BuOH/2-butanone (10 mL/5 mL). The mixture was stirred at 110° C. for 10 min, then cis-4-(1,1-difluoroethyl)cyclohexyl methanesulfonate(145 mg, 0.6 mmol, 1.1 eq.) was added to the mixture and the mixture was stirred at 110° C. for 15 h. Water was added to the mixture and the mixture was extracted with EtOAc. The organic layer was concentrated and purified by is silica gel column chromatography using petroleum ether/ethyl acetate (1/1) as eluent to give product (203 mg, 58%) as a slight yellow solid. EDI-MS (M+1): 390.1. 1H NMR (400 MHz, CDCl3) δ 7.75-7.72 (m, 3H), 7.42 (dd, 1H), 7.16-7.14 (m, 2H), 6.14 (s, 1H), 4.42 (s, 2H), 4.34-4.30 (m, 1H), 2.31-2.29 (m, 2H), 2.04-2.01 (m, 2H), 1.84 (s, 3H), 1.64-1.22 (m, 8H).

후처리

  1. stirringthe mixture was stirred at 110° C. for 15 h
  2. extractionthe mixture was extracted with EtOAc
  3. concentrationThe organic layer was concentrated
  4. custompurified

출처 및 근거

ORD 기록
ord-291e51850dd944e1a7ec0301e8817957
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546359B2

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