Triphenylphosphine → Methyl 3-((2-(N-t-Butyloxycarbonyl-N-methylamino)ethoxy))benzoate

HRID 259788

반응식

HRID 259788 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]([O:16][C:17]([N:19]([CH3:23])[CH2:20][CH2:21]O)=[O:18])([CH3:15])([CH3:14])[CH3:13].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:12]([O:16][C:17]([N:19]([CH2:20][CH2:21][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:23])=[O:18])([CH3:15])([CH3:14])[CH3:13]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 88068Methyl 3-HydroxybenzoateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

생성물 1

HCID 18930729Methyl 3-((2-(N-t-Butyloxycarbonyl-N-methylamino)ethoxy))benzoate수율 72.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 3-hydroxybenzoate (6.4 g, 42 mmol), alcohol 121a (7.4 g, 42 mmol), diisopropyl azodicarboxylate (8.3 mL, 42 mmol), and triphenylphosphine (11.1 g, 42 mmol) were stirred in dry THF (120 mL) at 0 ° C. for 1 h, then for 18 h at room temperature. After evaporation of solvent, the product was isolated by chromatography on silica gel, eluting with 0% to 30% EtOAc in hexane to yield a clear oil (9.4 g). IR(film) cm-1 1726, 1696. 1H NMR(300 MHz, CDCl3): 7.64-7.09 (m, 4H), 4.13 (m, 2H), 3.92 (s, 3H), 3.62 (br, 2H), 2.99 (s, 3H), 1.46 (s, 9H). Anal. Cald'd for C16H23NO5 : C, 62.11; H, 7.51; N, 4.53; Found: C, 61.67; H, 7.43; N, 4.47. HR-MS: Calc'd. 310.1654, Found 310.1650.

후처리

  1. customAfter evaporation of solvent
  2. customthe product was isolated by chromatography on silica gel
  3. washeluting with 0% to 30% EtOAc in hexane

출처 및 근거

ORD 기록
ord-92de8bfaa49944c8b84e9082495015b5
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05523302

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