Benzyl Bromide → Boc-DTrp-OBzl

HRID 2082210

반응식

HRID 2082210 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 10739405Boc-DTrp-OBzl수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b08df90ed268472484e2250dbf5f4ea9
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05187156

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