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

HRID 58900

反応式

HRID 58900 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
55 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-d81204e5ed364f4790ee10a56f8d230a
出典データセット
uspto-grants-2016_09
特許番号
US09434761B2

関連ノート

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