Diisopropylethylamine → HCID 89791481、化合物

HRID 470584ノート

反応式

HRID 470584 の反応式
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16](F)=[O:17])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:19]([CH:22]1[CH:31]([OH:32])[C:30]2[C:25](=[CH:26][C:27]([C:33](=[N:35]O)[NH2:34])=[CH:28][CH:29]=2)[O:24][CH2:23]1)=[N+:20]=[N-:21].CCN(C(C)C)C(C)C>C(#N)C>[N:19]([CH:22]1[CH:31]([OH:32])[C:30]2[C:25](=[CH:26][C:27]([C:33]3[N:35]=[C:16]([C:10]4[O:9][N:8]=[C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[C:11]=4[C:12]([F:15])([F:14])[F:13])[O:17][N:34]=3)=[CH:28][CH:29]=2)[O:24][CH2:23]1)=[N+:20]=[N-:21]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 58374067HCID 58374067、化合物HCID 131731134HCID 131731134、化合物

生成物 1

HCID 89791481HCID 89791481、化合物収率 59.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride Int-1-G (273 mg, 1.05 mmol) in ACN (6.7 mL) was added racemic (3R*,4S*,E/Z)-3-azido-N′,4-dihydroxychroman-7-carboximidamide (250 mg, 1.0 mmol) and Hunig's Base (210 μL, 1.2 mmol). The resulting solution was stirred overnight. Next, the solvent was evaporated. The resulting residue was purified by column chromatography (ISCO Combiflash Companion, 12 g silica gel, 10% ethyl acetate-hexane for 5 min then ramp to 50% ethyl acetate-hexane over 7 min then 50% ethyl acetate-hexane for 3 more min, product came out 8-10 min) to give racemic (3R*,4S*)-3-azido-7-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)chroman-4-ol (280 mg, 0.59 mmol, 59.3% yield): LCMS=470.98 [M+H]+, 1H NMR (400 MHz, CDCl3) δ ppm 7.82 (1H, dd, J=8.03, 1.65 Hz), 7.66-7.72 (3H, m), 7.52-7.62 (4H, m), 4.96-5.02 (1H, m), 4.43-4.51 (1H, m), 4.32-4.38 (1H, m), 4.08-4.17 (1H, m).

後処理

  1. customNext, the solvent was evaporated
  2. customThe resulting residue was purified by column chromatography (ISCO Combiflash Companion, 12 g silica gel, 10% ethyl acetate-hexane for 5 min
  3. waitthen ramp to 50% ethyl acetate-hexane over 7 min
  4. wait50% ethyl acetate-hexane for 3 more min, product came out 8-10 min

出典と根拠

ORDレコード
ord-bb5c5922425741c8ae9be2163c014092
出典データセット
uspto-grants-2014_01
特許番号
US08629282B2

反応ノート

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