Triethylamine → 4-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2,5-difluoro-3-methoxybenzoic acid ethyl ester

HRID 729373ノート

反応式

HRID 729373 の反応式
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([F:11])[C:8](F)=[C:7]([O:13][CH3:14])[C:6]=1[F:15])[CH3:2].[C:17]([O:21][C:22](=[O:29])[NH:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>C(#N)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:26]2[CH2:27][CH2:28][CH:24]([NH:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:29])[CH2:25]2)=[C:7]([O:13][CH3:14])[C:6]=1[F:15])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 2774387Benzoic acid, 2,4,5-trifluoro-3-methoxy-, ethyl ester

生成物 1

HCID 210411814-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2,5-difluoro-3-methoxybenzoic acid ethyl ester収率 77.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 2,4,5-trifluoro-3-methoxybenzoic acid ethyl ester (Example 1f, 2.821 g, 12.05 mmol), pyrrolidin-3-ylcarbamic acid tert-butyl ester (3.310 g, 17.77 mmol), and triethylamine (9.13 g, 12.6 mL, 90.23 mmol) in acetonitrile (50 mL) is heated at 40° C. under nitrogen for 2 days. The yellow solution is concentrated to near dryness and poured into saturated NaHCO3 solution and extracted with dichloromethane. The combined organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum. The resulting residue is purified by flash column chromatography (1:7 ethyl acetate/hexanes) to afford the title compound as a yellow solid (3.743 g). MS EI: m/z 401 (MH+).

後処理

  1. concentrationThe yellow solution is concentrated
  2. additionpoured into saturated NaHCO3 solution
  3. extractionextracted with dichloromethane
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe resulting residue is purified by flash column chromatography (1:7 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-85ae4794eb514dfd9e47e9337ad88c10
出典データセット
uspto-grants-2009_09
特許番号
US07582627B2

反応ノート

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