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Chloroform → N-lauroyl-L-valine cyclohexylamide

HRID 13725
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HRID 13725 반응식
[C:1]([NH:14][C@H:15]([C:19]([OH:21])=O)[CH:16]([CH3:18])[CH3:17])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O.ON1C(=O)CCC1=O.C(Cl)(Cl)Cl.[CH:35]1([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(OCC)(=O)C.C(N(CC)CC)C>[CH:35]1([NH:41][C:19](=[O:21])[C@H:15]([CH:16]([CH3:17])[CH3:18])[NH:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1
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참가 물질

7

반응물 4

HCID 6212ChloroformHCID 7965CyclohexylamineHCID 26658N-(1-Oxododecyl)-L-valineHCID 18987794N-Hydroxysuccinimide hydrate

생성물 1

HCID 11523764N-lauroyl-L-valine cyclohexylamide수율 44%

시약·촉매·용매 2

HCID 8471Triethylamine용매
HCID 8857Ethyl Acetate용매

실험 절차

61 mg (0.20 mmol) of N-lauroyl-L-valine and 39 mg (0.26 mmol) of N-hydroxysuccinimide monohydrate were dissolved into 3.0 mL of dried chloroform. 50 mg (0.26 mmol) of 1-ethyl-3-(3-dimethylpropyl)carbodiimide hydrochloride was added thereto under argon atmosphere and in the ice bath, and stirred at 0° C. for 3 hours. 35 μL of triethylamine and 35 μL of cyclohexylamine were added thereto and stirred at room temperature overnight. Then, 20 mL of ethyl acetate was added thereto and washed with 25 mL of 0.2N hydrochloric acid, 20 mL of water and 20 mL of a saturated aqueous solution of sodium hydrogen carbonate. The mixture was then dried with anhydrous sodium sulfate and condensed under reduced pressure. The residue was purified with a thin-layer chromatography (silica gel, chloroform:methanol=20:1) to obtain 34 mg of N-lauroyl-L-valine cyclohexylamide (0.089 mmol, yield 44%).

후처리

  1. washwashed with 25 mL of 0.2N hydrochloric acid, 20 mL of water and 20 mL of a saturated aqueous solution of sodium hydrogen carbonate
  2. dry with materialThe mixture was then dried with anhydrous sodium sulfate and condensed under reduced pressure
  3. customThe residue was purified with a thin-layer chromatography (silica gel, chloroform:methanol=20:1)

출처 및 근거

ORD 기록
ord-5ddb13722ece4107bca665ef961a4d5b
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728158B2

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