Potassium Carbonate → HCID 18697443, compound

HRID 1956099Notes

Reaction equation

HRID 1956099 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 (1×50 mL) and the combined organic layers were washed with NaCl solution (50 mL), dried with Na2 SO4 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 C33H52N2O4S2). 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 (1×50 mL)
  5. washthe combined organic layers were washed with NaCl solution (50 mL)
  6. customdried with Na2 SO4
  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-90c19ceea4fd42f8943455b34ba17f59
Source dataset
uspto-grants-1998_07
Patent number
US05780007

Reaction notes

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