Ethanolamine → HCID 19600242, 화합물

HRID 611257노트

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HRID 611257 반응식
[C:1]([C:9]1[CH:28]=[CH:27][C:12]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3[CH:21]=[C:22]([C:24](O)=[O:25])[O:23][C:17]=3[CH2:16]2)=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][CH2:30][CH2:31][OH:32].C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C(#N)C>[OH:32][CH2:31][CH2:30][NH:29][C:24]([C:22]1[O:23][C:17]2[CH2:16][N:15]([C:13](=[O:14])[C:12]3[CH:27]=[CH:28][C:9]([C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:10][CH:11]=3)[CH2:20][CH2:19][C:18]=2[CH:21]=1)=[O:25]

참가 물질

8

반응물 6

HCID 700EthanolamineHCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 19600266HCID 19600266, 화합물

생성물 1

HCID 19600242HCID 19600242, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 0.545 g (1.452 mmol) of 6-(4-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylic acid, 98 mg (1.6 mmol) of 2-aminoethanol, 0.61 ml (4.4 mmol) of triethylamine and 1.40 ml (14.5 mmol) of carbon tetrachloride in 20 ml of acetonitrile, 1.14 g (4.36 mmol) of triphenylphosphine was added under ice-cooling, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=9/1); the resulting solid was washed with diethyl ether to yield the desired product.

후처리

  1. temperaturecooling
  2. extractionextracted with ethyl acetate 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=9/1)
  6. washthe resulting solid was washed with diethyl ether

출처 및 근거

ORD 기록
ord-0fde3147b70742288e94cc35008d1e5d
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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