Water → HCID 22909970, compound

HRID 1379287Notes

Reaction equation

HRID 1379287 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11](Cl)=[O:12].[Br:16][C:17]1[CH:18]=[C:19]([N:24]2[CH2:28][CH2:27][CH:26]([NH:29]CC)[C:25]2=[O:32])[CH:20]=[CH:21][C:22]=1[F:23].O>ClCCl.C(OCC)C>[Br:16][C:17]1[CH:18]=[C:19]([N:24]2[CH2:28][CH2:27][CH:26]([NH:29][C:11](=[O:12])[CH2:10][C:9]([CH3:15])([CH3:14])[CH3:8])[C:25]2=[O:32])[CH:20]=[CH:21][C:22]=1[F:23]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 22909977HCID 22909977, compound

Product 1

HCID 22909970HCID 22909970, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.28 ml), followed by 3,3-dimethylbutanoyl chloride (0.46 ml) was added to a solution of 1(3-bromo-4-fluorophenyl)3-ethylaminopyrrolidin-2-one, (0.5 g, prepared as in Step 3 of Example 15) in dichloromethane. The mixture was stirred for three hours at room temperature, and then left to stand overnight. It was then poured into water and the mixture extracted with dichloromethane and the extract dried (magnesium sulphate) and evaporated to leave a yellow oil. This was dissolved in diethyl ether and the solution passed through a column of silica using ether as the eluent. Fractions of 25 ml were collected. Fractions 3-8 were combined and evaporated to give the title compound as a clear oil. The NMR, IR, and mass spectra of the product were consistent with the structure assigned.

Workup

  1. waitleft
  2. waitto stand overnight
  3. extractionthe mixture extracted with dichloromethane
  4. dry with materialthe extract dried (magnesium sulphate)
  5. customevaporated
  6. customto leave a yellow oil
  7. customFractions of 25 ml were collected
  8. customevaporated

Sources & evidence

ORD record
ord-97aa96b2e131476b9412a642044b52d2
Source dataset
uspto-grants-1997_09
Patent number
US05670656

Reaction notes

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