Sodium Chloride → N-(tert-Butoxycarbonyl)-3,4-dibenzyloxyphenylalanine benzyl ester

HRID 1090558

反応式

HRID 1090558 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:21]=[C:19]([OH:20])[C:17]([OH:18])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>CN(C)C=O>[CH2:22]([O:11][C:10](=[O:12])[C@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([O:20][CH2:13][C:14]2[CH:21]=[CH:19][CH:17]=[CH:16][CH:15]=2)[CH:21]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 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 148.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

21.12 g of N-(tert-butoxycarbonyl) DOPA was dissolved in 200 ml of dimethylformamide, and after 50 g of benzyl bromide and 40 g of potassium carbonate were added, the mixture was stirred at a room temperature for 40 hours. After the addition of 400 ml of sodium chloride aqueous solution, the reaction mixture was extracted with 500 ml of ethyl acetate, and the extract was washed twice with saturated sodium chloride aqueous solution, dried over magnesium sulfate, filtered, and concentrated under a reduced pressure. To the resulting residue was added hexane to crystallize the title compound, which was then washed, filtered and dried to obtain 30.0 g of the colorless crystals.

後処理

  1. extractionthe reaction mixture was extracted with 500 ml of ethyl acetate
  2. washthe extract was washed twice with saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under a reduced pressure
  6. additionTo the resulting residue was added hexane
  7. customto crystallize the title compound, which
  8. washwas then washed
  9. filtrationfiltered
  10. customdried

出典と根拠

ORDレコード
ord-50bc21331db2405ea641b77cf7744369
出典データセット
uspto-grants-1992_01
特許番号
US05081246

関連ノート

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