Triethylamine → (S)-3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl-2,3,5,6-tetrafluorobenzoic acid benzyl ester

HRID 729371

反応式

HRID 729371 の反応式
[CH2:1]([O:8][C:9](=[O:21])[C:10]1[C:15]([F:16])=[C:14]([F:17])[C:13](F)=[C:12]([F:19])[C:11]=1[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:29]([O:33][C:34](=[O:41])[NH:35][C@H:36]1[CH2:40][CH2:39][NH:38][CH2:37]1)([CH3:32])([CH3:31])[CH3:30]>C(#N)C>[CH2:1]([O:8][C:9](=[O:21])[C:10]1[C:11]([F:20])=[C:12]([F:19])[C:13]([N:38]2[CH2:39][CH2:40][C@H:36]([NH:35][C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:41])[CH2:37]2)=[C:14]([F:17])[C:15]=1[F:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 517856Pentafluorobenzoic acid, benzyl esterHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

生成物 1

HCID 86607128(S)-3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl-2,3,5,6-tetrafluorobenzoic acid benzyl ester収率 63.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 2,3,4,5,6-pentafluorobenzoic acid benzyl ester (Example 1d, 8.05 g, 26.6 mmol), triethylamine (26 mL, 186 mmol), and (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (5.6 g, 30 mmol) in acetonitrile (150 mL) is stirred at room temperature for 24 hours. The solvent is removed under vacuum and the residue dissolved in chloroform, washed with NaHCO3 and then brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford a solid. The solid is then purified by column chromatography (1:1:6 ethyl acetate/chloroform/hexanes) to yield the title compound as a solid (7.92 g). 1H NMR (CDCl3): δ 7.48-7.30 (m, 5H, 5.35 (s, 2H), 4.77-4.50 (m, 1H), 4.37-4.19 (m, 1H), 4.01-3.63 (m, 3H), 3.59-3.46 (m, 1H), 2.29-2.09 (m, 1H), 2.01-1.82 (m, 1H), 1.45 (s, 9H).

後処理

  1. customThe solvent is removed under vacuum
  2. dissolutionthe residue dissolved in chloroform
  3. washwashed with NaHCO3
  4. dry with materialbrine, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a solid
  8. customThe solid is then purified by column chromatography (1:1:6 ethyl acetate/chloroform/hexanes)

出典と根拠

ORDレコード
ord-af1fd9678bfe4bb2a9bfe583b721a5f8
出典データセット
uspto-grants-2009_09
特許番号
US07582627B2

関連ノート

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