Triethylamine → HCID 59619253, 화합물

HRID 1367596노트

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HRID 1367596 반응식
CO[C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:12])=[O:11])[CH2:7][C@@H:6]1[O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=[O:4].C[Al](C)C.C(N(CC)CC)C.Cl.[NH2:40][C:41]1([C:44]#[N:45])[CH2:43][CH2:42]1>C(Cl)Cl.[Cl-].[Na+].O>[C:44]([C:41]1([NH:40][C:3]([C@H:5]2[CH2:9][C@H:8]([S:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])(=[O:12])=[O:11])[CH2:7][C@@H:6]2[O:20][C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)=[O:4])[CH2:43][CH2:42]1)#[N:45]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 16682925TrimethylaluminumHCID 66918780HCID 66918780, 화합물

생성물 1

HCID 59619253HCID 59619253, 화합물수율 14.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

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온도
40 °C

실험 절차

To a solution of (1R,2R,4R) and (1S,2S,4S)-4-(2-chloro-benzenesulfonyl)-2-(4-chloro-phenoxy)-cyclopentanecarboxylic acid methyl ester (30 mg, 0.0699 mmol) in DCM (3 ml) was added trimethylaluminium (175 μl, 2M solution in toluene, 0.349 mmol), triethylamine (29.1 μl, 0.210 mmol) and 1-amino-1-cyclopropane-carbonitrile hydrochloride (21 mg, 0.1757 mmol) and the reaction mixture was stirred at 40° C. overnight. The mixture was then cooled to room temperature, diluted with brine and extracted 3 times with DCM. The combined organic layers were washed with water and brine, dried (Na2SO4) and evaporated. The remaining brown semisolid was purified by silica gel chromatography (DCM/MeOH 100:0-98:2) yielding a yellow solid (5 mg) that was triturated with ether to obtain the title compound (3 mg, 9%) as off-white solid. MS (EI): 477.0 (M+H)+.

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionextracted 3 times with DCM
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe remaining brown semisolid was purified by silica gel chromatography (DCM/MeOH 100:0-98:2)

출처 및 근거

ORD 기록
ord-9b59d7ad9caf4daaa1d6768584972928
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893099B2

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