تفاعل #685032

ord-e55cd67340af44ccab044c7506a21cfa

معادلة التفاعل

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

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe solvent was removed under reduced pressure
  2. 2
    workup.DISSOLUTIONthe residue dissolved in 150 ml of ethylacetate
  3. 3
    غسيلwashed three times with water
  4. 4
    تجفيفThe ethylacetate layer was dried with anhydrous sodium sulfate
  5. 5
    ترشيحfiltered
  6. 6
    أخرىthe ethylacetate removed under reduced pressure
  7. 7
    أخرىThe residue was purified by silica gel chromatography

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07897604B2uspto-grants-2011_03