N'-Hydroxybenzenecarboximidamide → HCID 46956711, 화합물

HRID 218323

반응식

HRID 218323 반응식
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]([OH:17])=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.O[N:61]=[C:62]([NH2:69])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>CN(C)C=O.O>[CH2:2]([N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[O:17][N:69]=[C:62]([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[N:61]=2)[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

8

반응물 5

HCID 69186N'-HydroxybenzenecarboximidamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27763524-Benzylmorpholine-2-carboxylic acid hydrochloride2회HCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 46956711HCID 46956711, 화합물수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 4-benzyl-2-morpholinecarboxylic acid hydrochloride (intermediate 20, 1.5 g, 5.82 mmol) in N,N-dimethylformamide (10 ml) was added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluroniumtetrafluoroborate (2.2 g, 6.98 mmol), 1-hydroxybenzotriazole hydrate (236 mg, 1.74 mmol) and N,N-diisopropylethylamine (5.1 ml, 29.1 mmol), and the reaction mixture was stirred at room temperature for 30 minutes. After the addition of N′-hydroxybenzamidine (792 mg, 5.82 mmol), the reaction mixture was stirred at room temperature for one hour, and then heated to 110° C. When the reaction was complete (checked by thin layer chromatography), excess reagent was decomposed by the addition of water and the aqueous layer was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel, (eluent; 25% ethyl acetate in hexane) to afford 4-benzyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)morpholine (intermediate 21, 1.44 g, 77%) as a colorless oil.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for one hour
  2. temperatureheated to 110° C
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography on silica gel, (eluent; 25% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-7841db3106c34e3c9282b61dd83d6901
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198437B2

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