Benzyl Bromide → N-(tert-Butoxycarbonyl)-3,4-dibenzyloxyphenylalanine benzyl ester

HRID 58900

반응식

HRID 58900 반응식
C([O-])([O-])=O.[K+].[K+].[C:7]([NH:14][C@@H:15]([CH2:19][C:20]1[CH:27]=[C:25]([OH:26])[C:23]([OH:24])=[CH:22][CH:21]=1)[C:16]([OH:18])=[O:17])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C>[CH2:28]([O:26][C:25]1[CH:27]=[C:20]([CH2:19][C@H:15]([NH:14][C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])[C:16]([O:18][CH2:19][C:20]2[CH:27]=[CH:25][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH:21]=[CH:22][C:23]=1[O:24][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14217229N-(tert-Buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine

생성물 1

HCID 22976099N-(tert-Butoxycarbonyl)-3,4-dibenzyloxyphenylalanine benzyl ester수율 163.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
55 °C

실험 절차

K2CO3 (21.0 g, 150 mmol) was added to a solution of Boc-L-dopa (10.0 g, 33 mmol) in acetonitrile (100 mL) followed by addition of benzyl bromide (21.0 g, 123 mmol). The suspension was heated at 50-60° C. for 4 h and then cooled to ambient temperature. The mixture was filtered and the filtration cake was washed with acetonitrile (50 mL). The filtrate and washings were combined and concentrated to dryness. The residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=20:1) to afford (S)-benzyl 3-(3,4-bis(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate (15.3 g, yield 80%).

후처리

  1. temperaturecooled to ambient temperature
  2. filtrationThe mixture was filtered
  3. washthe filtration cake was washed with acetonitrile (50 mL)
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=20:1)

출처 및 근거

ORD 기록
ord-d81204e5ed364f4790ee10a56f8d230a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434761B2

연결된 노트

불러오는 중…