Triethylamine → HCID 54205135, compound

HRID 420874Notes

Reaction equation

HRID 420874 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C@H:4]([CH2:21][SH:22])[NH:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9].C(N(CC)CC)C.[C:31](Cl)(=[O:40])[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:23])[C@H:4]([CH2:21][SH:22])[NH:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:19])[CH3:20])[CH3:14])[CH3:9].[CH3:1][O:2][C:3](=[O:23])[C@H:4]([CH2:21][SH:22])[N:5]([C:31](=[O:40])[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:19])[CH3:20])[CH3:14])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 54205135HCID 54205135, compound

Product 2

HCID 54205135HCID 54205135, compoundHCID 86634869HCID 86634869, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in 150 ml of ethylacetate
  3. washwashed three times with water
  4. dry with materialThe ethylacetate layer was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe ethylacetate removed under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f8e1cc831e04459699e3d57ae0aa89fe
Source dataset
uspto-grants-2012_01
Patent number
US08097722B2

Reaction notes

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