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Dicyclohexylcarbodiimide → Nalpha-[N-t-Butoxycarbonyl-3-(2-pyridyl)-D-alanyl]-1,beta-dimethyl-D-tryptophan methyl ester

HRID 2165561
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HRID 2165561 반응식
[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([C@H:6]([CH3:17])[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH3:16])[CH:8]=1)[NH2:5].[C:19]([O:23][C:24]([NH:26][C@@H:27]([C:35](O)=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([CH:6]([CH3:17])[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH3:16])[CH:8]=1)[NH:5][C:35](=[O:36])[C@@H:27]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[NH:26][C:24]([O:23][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:25]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 7019139(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(pyridin-2-yl)propanoic acidHCID 14151960(alphaR,betaR)-1,beta-dimethyltryptophan methyl ester

생성물 1

HCID 22841452Nalpha-[N-t-Butoxycarbonyl-3-(2-pyridyl)-D-alanyl]-1,beta-dimethyl-D-tryptophan methyl ester수율 85.3%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution of (αR,βR)-1,β-dimethyltryptophan methyl ester (6.36 g) and Nα -t-butoxycarbonyl-3-(2-pyridyl)-D-alanine (6.65 g) in dry methylene chloride (250 ml) was added dicyclohexylcarbodiimide (5.15 g), and resulting mixture was stirred for 1.5 hours at room temperature. After evaporation of the solvent, crude residue was taken up with ethyl acetate (200 ml), filtered, washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfate, treated with active charcoal, and evaporated. Nα -[N-t-Butoxycarbonyl-3-(2-pyridyl)-D-alanyl]-1,β-dimethyl-D-tryptophan methyl ester (10.54 g) was obtained as an oil.

후처리

  1. customresulting mixture
  2. customAfter evaporation of the solvent, crude residue
  3. filtrationfiltered
  4. washwashed with water and saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with active charcoal
  7. customevaporated

출처 및 근거

ORD 기록
ord-799ee53adb124315be91e8fb9226dc48
출처 데이터셋
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04940709

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