반응 #685032

ord-e55cd67340af44ccab044c7506a21cfa

반응 방정식

COC(=O)[C@H](CS)NCC=C(C)CCC=C(C)CCC=C(C)C
FCM
CCN(CC)CC
triethylamine
O=C(Cl)CCc1ccccc1
hydrocinnamoyl chloride
COC(=O)[C@H](CS)N(CC=C(C)CCC=C(C)CCC=C(C)C)C(=O)CCc1ccccc1
hydrocinnamoyl-farnesyl-L-Cysteine methyl ester
COC(=O)[C@H](CS)NCC=C(C)CCC=C(C)CCC=C(C)C
Farnesyl-L-Cysteine methyl ester

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The solvent was removed under reduced pressure
  2. 2
    workup.DISSOLUTIONthe residue dissolved in 150 ml of ethylacetate
  3. 3
    세척washed three times with water
  4. 4
    건조The ethylacetate layer was dried with anhydrous sodium sulfate
  5. 5
    여과filtered
  6. 6
    기타the ethylacetate removed under reduced pressure
  7. 7
    기타The residue was purified by silica gel chromatography

실험 절차

Farnesyl-L-Cysteine methyl ester (FCM) was synthesized as described in Ma et al., Methods Enzymol. 250, 226-34 (1995). The FCM (1 g) was dissolved in approximately 100 ml of acetone followed by the addition of triethylamine (TEA, 1 ml) and 1 g of hydrocinnamoyl chloride. This was stirred for 2 h at room temperature. The solvent was removed under reduced pressure, the residue dissolved in 150 ml of ethylacetate and washed three times with water. The ethylacetate layer was dried with anhydrous sodium sulfate, filtered and the ethylacetate removed under reduced pressure. The residue was purified by silica gel chromatography to obtain hydrocinnamoyl-farnesyl-L-Cysteine methyl ester (HCFCM). The purified HCFCM was then analyzed by Electron Spray Ionization Mass Spectrometry (ESI-MS).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07897604B2uspto-grants-2011_03