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Hydrochloric Acid → N-benzoyl-S-farnesylcysteine

HRID 1590448
ノート
印刷プレビュー

反応式

HRID 1590448 の反応式
[CH2:1]([S:16][CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.[OH-].[Na+]>C(OCC)(=O)C.C(N(CC)CC)C.CO>[C:23]([NH:19][C@H:18]([C:20]([OH:22])=[O:21])[CH2:17][S:16][CH2:1][CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 122323S-Farnesyl cysteine

生成物 1

HCID 54367624N-benzoyl-S-farnesylcysteine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 22036596
Ethyl acetate triethylamine
溶媒

実験手順

S-farnesylcysteine was dissolved in dry ethyl acetate/triethylamine in a dry flask under nitrogen. equivalents of benzoylchloride was added in the cold and the suspension was allowed to stir for an hour. The solution was neutralized with dilute HCl. After evaporation, the product was applied to a preparative thin layer chromatography plate and eluted with hexane/ethyl acetate. The pure product was removed from the plate and eluted with methanol. Yields were in the range of 50-75%. The product showed the anticipated nmr and infrared spectra. The parent acid was prepared from the ester by the addition of one equivalent of sodium hydroxide in methanol. The product showed the expected nmr and infrared spectra.

後処理

  1. customAfter evaporation
  2. washeluted with hexane/ethyl acetate
  3. customThe pure product was removed from the plate
  4. washeluted with methanol
  5. customYields

出典と根拠

ORDレコード
ord-b38c7273375c4c63987f915272276356
出典データセット
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05202456

反応ノート

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