tert-Butanol → Tert-butyl 4'-methoxy-4-biphenylcarbamate

HRID 493505

反応式

HRID 493505 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12](C(O)=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C([N:20]([CH2:23]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([NH:20][C:23]([O:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:32])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27595524'-Methoxy(1,1'-biphenyl)-4-carboxylic acid

生成物 1

HCID 68862395Tert-butyl 4'-methoxy-4-biphenylcarbamate収率 79%

実験手順

A mixture of 4′-methoxy-biphenyl-4-carboxylic acid (10.68 g, 46.8 mmol), prepared in the previous step, triethylamine (6.52 mL, 46.8 mmol) and diphenylphosphoryl azide (10.08 mL, 46.8 mmol) in 200 mL of tert-butyl alcohol was refluxed under nitrogen for 7 h and then stood overnight at room temperature. The tert-butyl alcohol was removed under reduced pressure. The residue was dissolved in methylene chloride, extracted with 1 N HCl, 1 N NaOH, dried (MgSO4) and the solvent removed under reduced pressure to give tert-butyl 4′-methoxy-4-biphenylcarbamate (11.1 g, 79%) as a white solid, mp 142-147° C., MS (ESI) m/z 300 [M+H]+. Elemental Analysis for C18H21NO3: Calc'd: C, 72.22; H, 7.07; N, 4.68; Found: C, 71.25; H, 6.92; N, 4.74.

後処理

  1. temperaturewas refluxed under nitrogen for 7 h
  2. customThe tert-butyl alcohol was removed under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. extractionextracted with 1 N HCl, 1 N NaOH
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-bd2a33c5ab984a6aade9376b117266cc
出典データセット
uspto-grants-2009_05
特許番号
US07534894B2

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