Benzyl Bromide → N-Benzyl-N-((benzyloxy)carbonyl)-beta-alanine

HRID 535028

反応式

HRID 535028 の反応式
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.CN(C=O)C>[CH2:19]([N:11]([C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 75313N-Benzyloxycarbonyl-beta-alanine

生成物 1

HCID 15547327N-Benzyl-N-((benzyloxy)carbonyl)-beta-alanine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of N-benzyloxycarbonyl-β-alanine (11.16 g, 50.00 mmol) in anhydrous THF (160 mL) and DMF (40 mL) at 0° C. was slowly added NaH (60% in oil, 6.000 g, 150.0 mmol). After stirring at 0° C. for 15 min, benzyl bromide (9.10 mL, 75.00 mmol) was added. The reaction mixture was stirred at rt for 22 h. It was quenched with water (90 mL), followed by 1 N HCl (110 mL), and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by Combiflash (40-60% EtOAc/hexane) to afford 3-{benzyl[(benzyloxy)cabonyl]amino}propanoic acid as a viscous pale yellow oil (14.2 g, 91% in yield). MS (ESI): 312.0 (M−H).

後処理

  1. customat 0° C.
  2. stirringThe reaction mixture was stirred at rt for 22 h
  3. customIt was quenched with water (90 mL)
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by Combiflash (40-60% EtOAc/hexane)
  10. customto afford

出典と根拠

ORDレコード
ord-f1fd0a315e02460294dd9dc28ec59c10
出典データセット
uspto-grants-2014_10
特許番号
US08853243B2

関連ノート

読み込み中…