Triphenylphosphine → 5-{3-(3-(3-Hydroxy-2-methoxycarbonyl-phenoxy)-propyl)-phenyl}-isoxazole-3-carboxylic Acid

HRID 1375666노트

반응식

HRID 1375666 반응식
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][OH:20])[CH:12]=2)[O:8][N:7]=1)=[O:5])C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:40][C:41]1[CH:50]=[CH:49][CH:48]=[C:47](O)[C:42]=1[C:43]([O:45][CH3:46])=[O:44].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[OH:40][C:41]1[C:42]([C:43]([O:45][CH3:46])=[O:44])=[C:47]([CH:48]=[CH:49][CH:50]=1)[O:20][CH2:19][CH2:18][CH2:17][C:13]1[CH:12]=[C:11]([C:9]2[O:8][N:7]=[C:6]([C:4]([OH:3])=[O:5])[CH:10]=2)[CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 519869Methyl 2,6-dihydroxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 695081845-(3-(3-Hydroxy-propyl)-phenyl)-isoxazole-3-carboxylic Acid Ethyl Ester

생성물 1

HCID 100463425-{3-(3-(3-Hydroxy-2-methoxycarbonyl-phenoxy)-propyl)-phenyl}-isoxazole-3-carboxylic Acid수율 7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 5-(3-(3-hydroxy-propyl)-phenyl)-isoxazole-3-carboxylic acid ethyl ester (31 mg, 0.1 mmol) was added triphenylphosphine (29 mg, 0.11 mmol), methyl (2,6-dihydroxy)benzoate (20 mg, 0.12 mmol), then THF (1 mL). After the solids had dissolved, diethylazodicarboxylate (20 μL, 0.13 mmol) was added, and the reaction was stirred at ambient temperature for 1 hour. The reaction was concentrated in vacuo, and the residue was taken up in aqueous 2M NaOH (1 mL), along with enough methanol to make the solution homogeneous. After stirring for 10 minutes, the solvents were removed in vacuo, glacial acetic acid (4 drops)was added, and the product was purified by reverse phase HPLC, eluting with a acetonitrile/0.1% aq. trifluoroacetic acid gradient to provide the title compound (2.7 mg, 7%). 1H NMR (500 MHz, d6-DMSO) δ 9.94 (s, 1H), 7.79 (s, 1H), 7.76 (d, 1H, J=7.8 Hz), 7.46 (t, 1H, J=7.6 Hz), 7.37 (d, 1H, J=7.5 Hz), 7.34 (s, 1H), 7.15 (t, 1H, J=8.3 Hz), 6.49 (dd, 2H, J=2.8, 8.4 Hz), 3.95 (t, 2H, J=6.2 Hz), 3.79 (s, 3H), 2.78 (t, 2H, J=7.5 Hz), 2.01 (m, 2H); MS (ESI) m/z 398 (M+H), 415 (M+NH4).

후처리

  1. dissolutionAfter the solids had dissolved
  2. concentrationThe reaction was concentrated in vacuo
  3. stirringAfter stirring for 10 minutes
  4. customthe solvents were removed in vacuo, glacial acetic acid (4 drops)
  5. additionwas added
  6. customthe product was purified by reverse phase HPLC
  7. washeluting with a acetonitrile/0.1% aq. trifluoroacetic acid gradient

출처 및 근거

ORD 기록
ord-e5de3e5c7dff419e88fba206cb834224
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169797B2

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