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Chloroform → N-lauroyl-L-valine cyclohexylamide

HRID 13725
ノート
印刷プレビュー

反応式

HRID 13725 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

HCID 11523764N-lauroyl-L-valine cyclohexylamide収率 44%

試薬・触媒・溶媒 2

HCID 8471Triethylamine溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5ddb13722ece4107bca665ef961a4d5b
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07728158B2

反応ノート

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