Benzyl Bromide → Boc-DTrp-OBzl

HRID 2082210

反応式

HRID 2082210 の反応式
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13]([O:15][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 111050N-((tert-Butoxy)carbonyl)-D-tryptophan

生成物 1

HCID 10739405Boc-DTrp-OBzl収率 95%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To an ice-cooled solution of Boc-D-Trp-OH (8.61 g) in DMF (100 ml) were added benzyl bromide (7.19 g) and diisopropylethylamine (4.02 g). The solution was stirred for two hours at the same temperature and overnight at room temperature. After evaporation, the residue was extracted with ethyl acetate. The organic layer was washed successively with water, sodium hydrogencarbonate solution, 0.5 hydrochlolic acid, and sodium chloride solution, and dried over magnesium sulfate. Evaporation gave Boc-D-Trp-OBzl (10.6 g) as a crystalline mass.

後処理

  1. customAfter evaporation
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water, sodium hydrogencarbonate solution, 0.5 hydrochlolic acid, and sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation

出典と根拠

ORDレコード
ord-b08df90ed268472484e2250dbf5f4ea9
出典データセット
uspto-grants-1993_02
特許番号
US05187156

関連ノート

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