Lithium Hydroxide → N-(2,2-Diphenyl-ethyl)-2-hydroxy-N-methyl-2-phenyl-acetamide

HRID 1410375ノート

反応式

HRID 1410375 の反応式
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][NH:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([ClH][C:21](=[O:30])[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[OH:23])(=O)C.C(N(CC)CC)C.[OH-].[Li+]>C(Cl)(Cl)Cl.O1CCCC1.CO>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][N:9]([CH3:10])[C:21](=[O:30])[CH:22]([OH:23])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

6

反応物 3

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 12914583N-Methyl-2,2-diphenylethan-1-amine

生成物 1

HCID 22174856N-(2,2-Diphenyl-ethyl)-2-hydroxy-N-methyl-2-phenyl-acetamide収率 93.5%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a stirred solution of (2,2-diphenylethyl)methylamine (4.97 g, 23.5 mmol) in chloroform (50 mL) was added O-acetylmandelic chloride (5.3 mL, 24 mmol) followed by triethylamine (4.0 mL, 29 mmol). The reaction was stirred for 1 hour and then concentrated. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford a colorless gum. The crude amide was taken up in 1:1 tetrahydrofuran/methanol (80 mL) and treated with 1 N aqueous lithium hydroxide (30 mL, 30 mmol). The mixture was stirred for 2 hours and concentrated to remove the organic solvents. The remaining aqueous solution was diluted with water and extracted twice with ethyl acetate and once with methylene chloride. The combined organic extracts were dried (sodium sulfate) and concentrated to afford an off-white solid. This material was triturated with diethyl ether to afford 7.59 g (93%) of product as a white solid: 1H NMR (CDCl3) δ 7.43-6.98 (m, 15H), 5.07 (s, 1H), 4.57-4.44 (m, 1H), 4.36-4.28 (m, 1H), 3.76-3.64 (m, 1H), 2.46 (s, 3H) ppm.

後処理

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. customto afford a colorless gum
  6. stirringThe mixture was stirred for 2 hours
  7. concentrationconcentrated
  8. customto remove the organic solvents
  9. additionThe remaining aqueous solution was diluted with water
  10. extractionextracted twice with ethyl acetate and once with methylene chloride
  11. dry with materialThe combined organic extracts were dried (sodium sulfate)
  12. concentrationconcentrated
  13. customto afford an off-white solid
  14. customThis material was triturated with diethyl ether

出典と根拠

ORDレコード
ord-f8c6aa7691394ba2ad107a5a8658c16e
出典データセット
uspto-grants-2014_12
特許番号
US08921547B2

反応ノート

読み込み中…