Diisopropylethylamine → HCID 89791481, 화합물

HRID 470584노트

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HRID 470584 반응식
[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]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 58374067HCID 58374067, 화합물HCID 131731134HCID 131731134, 화합물

생성물 1

HCID 89791481HCID 89791481, 화합물수율 59.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bb5c5922425741c8ae9be2163c014092
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629282B2

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