Dimethylformamide → HCID 56942733, compound

HRID 467987Notes

Reaction equation

HRID 467987 reaction equation
C(OC(=O)[CH:5]([CH:25]1[CH2:27][CH2:26]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH:22]1CC1)C(O)=O)C.C(Cl)(=O)C(Cl)=O.C[N:36]([CH:38]=[O:39])C.[C:40]([O:43][CH2:44][CH3:45])(=[O:42])C>ClCCl>[CH2:44]([O:43][C:40]([C:17]1([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:25]2([C:38](=[O:39])[NH2:36])[CH2:26][CH2:27]2)[CH2:18][CH2:22]1)=[O:42])[CH3:45]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 66795682HCID 66795682, compound

Product 1

HCID 56942733HCID 56942733, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of product of Example 9 (1.5 g, 4.09 mmol) in dichloromethane (15 mL) was added oxalyl chloride (0.68 mL, 8.1 mmol) and catalytic amount of DMF (0.015 mL) at ice temperature. The ice bath was removed and reaction mixture stirred at room temperature over a period of 1 h. The crude product obtained upon evaporation of the solvent was diluted with DCM (10 mL), cooled to ice bath temperature and added ammoniated DCM (100 mL) drop wise fashion. Then reaction mixture was slowly allowed to reach room temperature and stirred for 2 h. The resulting reaction mass was diluted with ethyl acetate (250 mL), washed with water (100 mL×2) and dried over sodium sulphate. The residue obtained upon evaporation of the volatiles was purified by silica gel (230-400) column (40% ethyl acetate in petroleum ether) to give product as yellow oil 0.84 g (56%). The pale yellow oil solidified as off-white solid upon storage. mp: 49.5-51.2.2° C.

Workup

  1. customThe ice bath was removed
  2. customreaction mixture
  3. customThe crude product obtained upon evaporation of the solvent
  4. temperaturecooled to ice bath temperature
  5. customThen reaction mixture
  6. customto reach room temperature
  7. stirringstirred for 2 h
  8. customThe resulting reaction mass
  9. washwashed with water (100 mL×2)
  10. dry with materialdried over sodium sulphate
  11. customThe residue obtained upon evaporation of the volatiles
  12. customwas purified by silica gel (230-400) column (40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-2bbee8b7e5104e69908922a193665fe1
Source dataset
uspto-grants-2014_01
Patent number
US08623897B2

Reaction notes

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