Water → HCID 20621501, compound

HRID 2120369Notes

Reaction equation

HRID 2120369 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:13])[F:12])=[C:4]([Cl:18])[C:3]=1[Cl:19].[SH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1.CCOC(C)=O.O>CN(C=O)C>[C:25]([C:24]1[CH:28]=[CH:29][C:21]([S:20][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:13])[F:12])=[C:4]([Cl:18])[C:3]=2[Cl:19])=[CH:22][CH:23]=1)([OH:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 957384-Mercaptobenzoic acidHCID 69824119HCID 69824119, compound

Product 1

HCID 20621501HCID 20621501, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-N-[4-Iodo-2,3-dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 4) (4.58 g, 10.7 mmol) was heated in DMF (30 ml) with stirring under argon for 4 hours with 4-mercaptobenzoic acid (2.31 g, 14.98 mmol) and cuprous oxide (765 mg) and allowed to cool to room temp. EtOAc and water were added, and the reaction mixture was filtered through a bed of diatomaceous earth, and washed with EtOAc/water. The organic layer was separated, washed with water, brine, dried and evaporated down to dryness. The resulting solid was purified using a Mega Bond Elut column, eluting with 5-50% EtOAc/isohexane to give the title compound (4.0 g) as a pale pink solid. NMR: 1.6 (s, 3H), 7.3 (d, 2H), 7.5 (d, 1H), 7.9 (m, 3H), 8.0 (d, 1H), 9.9 (s, 1H), 13.0 (s, 1H); m/z: 452.

Workup

  1. filtrationthe reaction mixture was filtered through a bed of diatomaceous earth
  2. washwashed with EtOAc/water
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. customdried
  6. customevaporated down to dryness
  7. customThe resulting solid was purified
  8. washeluting with 5-50% EtOAc/isohexane

Sources & evidence

ORD record
ord-06f9a6128426433286e944ce94c08612
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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