Imidazole → (aR)-a-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzeneacetic Acid

HRID 454980ノート

反応式

HRID 454980 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2 回HCID 11821572Boc-4-hydroxy-D-phenylglycine

生成物 1

HCID 86658147(aR)-a-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzeneacetic Acid収率 123.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (R)-tert Butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid (2.54 g, 9.55 mmol) in DMF (5 mL) was added imidazole (1.43 g, 21 mmol) followed by t-butyldimethylsilyl chloride (1.58 g, 10.5 mmol). The resulting mixture was stirred at rt for overnight. Additional t-butyldimethylsilyl chloride (1.43 g, 9.55 mmol) was added and let the reaction continue for another hour. The reaction mixture was diluted with EtOAc and washed with H2O three times and concentrated. To the residue was added aqueous 1N NaOH and then acidified with concentrated HCl. The resulting mixture was extracted with EtOAc three times. The combined organic layer was dried (MgSO4) and concentrated to provide the titled compound (4.5 g).

後処理

  1. waitcontinue for another hour
  2. washwashed with H2O three times
  3. concentrationconcentrated
  4. additionTo the residue was added aqueous 1N NaOH
  5. extractionThe resulting mixture was extracted with EtOAc three times
  6. dry with materialThe combined organic layer was dried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-2a1287e2a01740aa9b86ce2706ea1673
出典データセット
uspto-grants-2013_07
特許番号
US08497271B2

反応ノート

読み込み中…