Iodoethane → HCID 69883800, compound

HRID 2120358Notes

Reaction equation

HRID 2120358 reaction equation
C(N[C:5]1[C:6]([Cl:34])=[C:7]([NH:24][C:25](=[O:33])[C@:26]([OH:32])([CH3:31])[C:27]([F:30])([F:29])[F:28])[CH:8]=[CH:9][C:10]=1[S:11]([C:14]1C=CC(NCCO)=C[CH:15]=1)(=O)=O)(=O)C.C[O-].[Na+].C([I:40])C.CCOC(C)=O>C1COCC1>[CH2:14]([S:11][C:10]1[CH:9]=[CH:8][C:7]([NH:24][C:25](=[O:33])[C@:26]([OH:32])([CH3:31])[C:27]([F:30])([F:29])[F:28])=[C:6]([Cl:34])[C:5]=1[I:40])[CH3:15]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 69882922HCID 69882922, compound

Product 1

HCID 69883800HCID 69883800, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-N-[4-mercapto-3-iodo-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 29) (5.85 g) in anhydrous THF (40 ml) under argon was added sodium methoxide (0.44 g) followed by ethyl iodide (0.65 ml) and the mixture was heated under reflux for 1 hour and allowed to cool to ambient temperature. EtOAc (200 ml) was added, the organic phase was washed with brine (100 ml) and dried. Volatile material was removed by evaporation and the residue was purified by flash column chromatography eluting with 5-30% EtOAc/isohexane to give the title compound (2.08 g) as a pale yellow solid. NMR (CDCl3) 1.36 (t, 3H), 1.75 (s, 3H), 2.92-2.99 (q, 2H), 7.15 (d, 1H), 8.34 (d, 1H), 8.89 (s, 1H); m/z: 452.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. washthe organic phase was washed with brine (100 ml)
  4. customdried
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by flash column chromatography
  7. washeluting with 5-30% EtOAc/isohexane

Sources & evidence

ORD record
ord-e75ced233e6d43cdbb45df8e911abd67
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

Loading…