Potassium Carbonate → HCID 18697443, compound

HRID 863366Notes

Reaction equation

HRID 863366 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][S:8][C:9]([CH3:30])([CH3:29])[CH2:10][NH:11][CH2:12][CH2:13][NH:14][CH2:15][C:16]([CH3:28])([S:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH3:17])=[CH:5][CH:4]=1.[C:33]([O-])([O-])=O.[K+].[K+].Br[CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45]>CC#N>[C:44]([CH2:43][CH2:42][CH2:41][CH2:40][CH2:33][N:14]([CH2:15][C:16]([S:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)([CH3:28])[CH3:17])[CH2:13][CH2:12][NH:11][CH2:10][C:9]([CH3:30])([S:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:32][CH:31]=1)[CH3:29])([O:46][CH2:47][CH3:48])=[O:45]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 15408476HCID 15408476, compound

Product 1

HCID 18697443HCID 18697443, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To N,N'-bis-[2-(4-methoxybenzylthio)-2-methylpropyl]-ethylenediamine (4.13 g, 8.66 mmol) in CH3CN (50 mL) was added K2CO3 (1.21 g, 8.75 mmol, 101 mol %) followed by ethyl 5-bromovalerate (2.80 mL, 17.7 mmol, 204 mol %). The reaction was stirred at reflux overnight and was then concentrated to a paste in vacuo. The residue was partitioned between ethyl acetate (100 mL) and 0.5M KOH (100 mL). The aqueous layer was extracted with ethyl acetate (1x 50 mL) and the combined organic layers were washed with NaCl solution (50 mL), dried with Na2SO4 and concentrated to a yellow oil (~6 g). Purification by normal-phase preparative HPLC (100% CHCl3 to 5% methanol/chloroform over 25 min.) afforded pure title compound (1.759 g, 34% yield). FABMS analysis gave an (MH+) of 605 (compared with the value of 604.90 calculated for C33 H52N2O4S2). Nuclear magnetic resonance characterization experiments yielded the following molecular signature:

Workup

  1. temperatureat reflux overnight
  2. concentrationwas then concentrated to a paste in vacuo
  3. customThe residue was partitioned between ethyl acetate (100 mL) and 0.5M KOH (100 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (1x 50 mL)
  5. washthe combined organic layers were washed with NaCl solution (50 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated to a yellow oil (~6 g)
  8. customPurification by normal-phase preparative HPLC (100% CHCl3 to 5% methanol/chloroform over 25 min.)

Sources & evidence

ORD record
ord-afadbc12ed214a9ead7b9215537f046b
Source dataset
uspto-grants-1998_02
Patent number
US05720934

Reaction notes

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