Triphenylphosphine → HCID 69598041, 화합물

HRID 724617

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HRID 724617 반응식
[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](OCCCO)[CH:12]=2)[S:6]1(=[O:23])=[O:22])([CH3:4])([CH3:3])[CH3:2].[OH:24][C:25]1[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[C:26]=1[C:27]([O:29][CH3:30])=[O:28].[C:36]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:41]=CC=C[CH:37]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:30][O:29][C:27](=[O:28])[C:26]1[C:25]([OH:24])=[CH:34][CH:33]=[CH:32][C:31]=1[O:35][CH2:37][CH2:36][CH2:41][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:7]2[S:6](=[O:22])(=[O:23])[N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:9](=[O:10])[CH:8]=2)[CH:12]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 519869Methyl 2,6-dihydroxybenzoateHCID 58746837HCID 58746837, 화합물

생성물 1

HCID 69598041HCID 69598041, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

A solution of 4.08-C (0.21 g, 0.6 mmol), methyl 2,6-dihydroxybenzoate (0.13 g, 0.8 mmol), and triphenylphosphine (0.22 g, 0.8 mmol) in tetrahydrofuran (1.5 mL) was treated with diisopropyl azodicarboxylate (0.18 mL, 0.9 mmol) dropwise at 0° C. The reaction mixture was stirred at 25° C. for 2 h. The reaction mixture was concentrated to give a crude residue which was purified using flash column chromatography (100% hexane to 25% ethyl acetate/hexane) to yield 4.08-D as a white solid (0.18 g, 60%). 1H NMR (500 MHz, CDCl3): δ 11.47 (s, 1H), 7.42 (dd, J=8.3, 8.3 Hz, 1H), 7.34–7.31 (m, 3H), 7.11–7.08 (m, 1H), 6.62 (s, 1H), 6.60 (dd, J=8.3, 1.0 Hz, 1H), 6.43 (dd, J=8.3, 1.0 Hz, 1H), 4.27–4.25 (m, 2H), 4.21–4.19 (m, 2H), 3.91 (s, 3H), 2.33–2.30 (m, 2H), 1.73 (s, 9H); LCMS found for C24H27NO8SNa (M+Na)+: m/z=512.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customto give a crude residue which
  3. customwas purified
  4. customto yield 4.08-D as a white solid (0.18 g, 60%)

출처 및 근거

ORD 기록
ord-4e37e175629544f8a22e747b43485298
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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