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

HRID 1598813ノート

反応式

HRID 1598813 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-182c2ae24b424dc9a8453b3c352f73cd
出典データセット
uspto-grants-1998_04
特許番号
US05739163

反応ノート

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