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Dicyclohexylcarbodiimide → Boc-Gly-Lys(Z)-OBzl

HRID 1588475
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HRID 1588475 반응식
[NH2:1][C@H:2]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Cl.[NH:29]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][C:31](O)=[O:32].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O.C(N(CC)CC)C>[NH:29]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][C:31]([NH:1][C@H:2]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])=[O:32]
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참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 11750132L-Lysine, N6-((phenylmethoxy)carbonyl)-, phenylmethyl ester, hydrochloride (1:1)

생성물 1

HCID 14154103Boc-Gly-Lys(Z)-OBzl수율 80%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
2회
HCID 8471Triethylamine용매

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온도
4 °C

실험 절차

To a solution of 20.35 g of H-Lys(Z)-OBzl·HCl (manufactured by Kokusan Kagaku) in 35 ml of dimethylformamide (called DMF hereinbelow), after neutralized by addition under cooling with ice of 7 ml of triethylamine, were added 8.76 g of Boc-Gly-OH (manufactured by Kokusan Kagaku), 7.43 g of HOBt (manufactured by Kokusan Kagaku) and 11.35 g of DCC (manufactured by Kokusan Kagaku). The mixture was stirred for 3 hours and at 4° C. for additional 16 hours. Dicyclohexylurea by-product was removed by filtration followed by addition of 300 ml of ethyl acetate. The resulting mixture was washed successively with saturated aqueous sodium chloride, 8% by weight aqueous sodium carbonate, saturated aqueous sodium chloride, 8% by weight aqueous citric acid and saturated aqueous sodium chloride. From the ethyl acetate layer, after dried over anhydrous sodium sulfate, was removed the solvent, and the residue was again dissolved in a small amount of ethyl acetate. From the solution after filtered, the solvent was completely distilled off to give 21.1 g (80% yield) of Boc-Gly-Lys(Z)-OBzl as an oily substance.

후처리

  1. additionafter neutralized by addition
  2. customDicyclohexylurea by-product was removed by filtration
  3. additionfollowed by addition of 300 ml of ethyl acetate
  4. washThe resulting mixture was washed successively with saturated aqueous sodium chloride, 8% by weight aqueous sodium carbonate, saturated aqueous sodium chloride, 8% by weight aqueous citric acid and saturated aqueous sodium chloride
  5. dry with materialFrom the ethyl acetate layer, after dried over anhydrous sodium sulfate
  6. customwas removed the solvent
  7. dissolutionthe residue was again dissolved in a small amount of ethyl acetate
  8. filtrationFrom the solution after filtered
  9. distillationthe solvent was completely distilled off

출처 및 근거

ORD 기록
ord-c4f556557b0e457a907fa36b61987f3a
출처 데이터셋
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05223487

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