Diisopropylethylamine → Ethyl(2S)-3-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate

HRID 1725216노트

반응식

HRID 1725216 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][NH:7][CH2:8][CH3:9])=[CH:4][CH:3]=1.[CH2:12]([O:14][C@H:15]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:16][C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]([OH:25])=O)=[CH:19][CH:18]=1)[CH3:13].C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:8][CH3:9])[C:23](=[O:25])[CH2:22][O:21][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][C@H:15]([O:14][CH2:12][CH3:13])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:27][CH:26]=2)=[CH:10][CH:11]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 580651N-Ethyl-4-chlorobenzylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11162260{4-[(2S)-2,3-Diethoxy-3-oxopropyl]phenoxy}acetic Acid

생성물 1

HCID 68856731Ethyl(2S)-3-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate수율 61%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N-(4-chlorobenzyl)-N-ethylamine (0.150 g, 0.88 mmol) and {4-[(2S)-2,3-diethoxy-3-oxopropyl]phenoxy}acetic acid (0.270 g, 0.91 mmol) in methylene chloride (10 mL) were added N,N-diisopropylethylamine (0.34 mL, 1.9 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.320 g, 1.00 mmol) and the reaction mixture was stirred at room temperature overnight. The resulting solution was diluted with methylene chloride (40 mL) and the organic phase was washed with 5% HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL), dried over Na2SO4, and concentrated in vacuo. Purification on a prepacked column of silica gel (Isolute® SPE Column, 50 g/150 mL) with methylene chloride/ethyl acetate 10:1 as the eluent yielded 0.24 g (61%) of a colourless oil.

후처리

  1. washthe organic phase was washed with 5% HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification on a prepacked column of silica gel (Isolute® SPE Column, 50 g/150 mL) with methylene chloride/ethyl acetate 10:1 as the eluent

출처 및 근거

ORD 기록
ord-80b06cd52db54ba0bd2486defbabf092
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488844B2

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