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

HRID 729375

反応式

HRID 729375 の反応式
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([F:12])[C:6]=1[F:13])[CH3:2].[C:15]([O:19][C:20](=[O:27])[NH:21][CH:22]1[CH2:26][CH2:25][NH:24][CH2:23]1)([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>C(#N)C>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([N:24]2[CH2:25][CH2:26][CH:22]([NH:21][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:27])[CH2:23]2)=[C:7]([F:12])[C:6]=1[F:13])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 594559Benzoic acid, 2,3,4-trifluoro-, ethyl esterHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

生成物 1

HCID 210411774-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2,3-difluorobenzoic acid ethyl ester収率 70.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 2,3,4-trifluorobenzoic acid ethyl ester (Example 1g, 3.70 g, 18.1 mmol), pyrrolidin-3-ylcarbamic acid tert-butyl ester (4.02 g, 21.6 mmol), and triethylamine (18.0 mL, 129 mmol) in acetonitrile (50 mL) is heated at 50° C. under nitrogen atmosphere for 4.5 hours. The solution is concentrated in vacuo and poured into a saturated NaHCO3 solution. The mixture is then extracted with chloroform, and the combined organic extracts are washed with brine, dried with Na2SO4, filtered, and the mixture concentrated in vacuo. The resulting residue is then purified by column chromatography (1:7 ethyl acetate/hexanes) to afford the title compound (4.70 g). 1H NMR (CDCl3): δ 7.59-7.49 (m, 1H), 6.35-6.26 (m, 1H), 4.88-4.84 (bd, 1H), 4.39-4.28 (m, 3H), 3.81-3.50 (m, 3H), 3.48-3.34 (m, 1H), 2.32-2.15 (m, 1H), 2.02-1.76 (m, 1), 1.45 (s, 9H), 1.40 (t, 3H).

後処理

  1. concentrationThe solution is concentrated in vacuo
  2. additionpoured into a saturated NaHCO3 solution
  3. extractionThe mixture is then extracted with chloroform
  4. washthe combined organic extracts are washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationthe mixture concentrated in vacuo
  8. customThe resulting residue is then purified by column chromatography (1:7 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-f49dc76902a443e481d6c56e12b1a632
出典データセット
uspto-grants-2009_09
特許番号
US07582627B2

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