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

HRID 535028

반응식

HRID 535028 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f1fd0a315e02460294dd9dc28ec59c10
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853243B2

연결된 노트

불러오는 중…