Triethylamine → HCID 59619253、化合物

HRID 1367596ノート

反応式

HRID 1367596 の反応式
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]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 16682925TrimethylaluminumHCID 66918780HCID 66918780、化合物

生成物 1

HCID 59619253HCID 59619253、化合物収率 14.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
40 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-9b59d7ad9caf4daaa1d6768584972928
出典データセット
uspto-grants-2011_02
特許番号
US07893099B2

反応ノート

読み込み中…