Water → HCID 59619464, 화합물

HRID 1367480노트

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HRID 1367480 반응식
[C:1]([C:3]1([NH:6][C:7]([C@H:9]2[CH2:13][C@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20](F)=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@@H:10]2[O:25][CH3:26])=[O:8])[CH2:5][CH2:4]1)#[N:2].[F:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:1]([C:3]1([NH:6][C:7]([C@H:9]2[CH2:13][C@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([O:34][C:31]4[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=4)=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@@H:10]2[O:25][CH3:26])=[O:8])[CH2:5][CH2:4]1)#[N:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 59619199HCID 59619199, 화합물

생성물 1

HCID 59619464HCID 59619464, 화합물수율 68.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

(1R,2R,4R) and (1S,2S,4S)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (25 mg, 0.062 mmol, example 56) was dissolved in DMF (1.5 ml) and 4-fluorophenol (14 mg, 0.125 mmol) and Cs2CO3 (61 mg, 0.187 mmol) were added. The reaction mixture was stirred for 4 h at 50° C. Then water was added and the mixture was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated. The remaining residue was purified by silica gel chromatography (DCM/EtOAc 9:1) to obtain the title compound (21 mg, 63%) as white solid. MS (EI): 491.1 (M−H)−.

후처리

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe remaining residue was purified by silica gel chromatography (DCM/EtOAc 9:1)

출처 및 근거

ORD 기록
ord-0ae88e00996e4a71b5ea0a4b9571050b
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893099B2

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