Ethyl Acetate → HCID 69883377, compound

HRID 2120368Notes

Reaction equation

HRID 2120368 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][C:12]1[C:17]([Cl:18])=[C:16](I)[CH:15]=[CH:14][C:13]=1[NH:20][C:21](=[O:29])[C@:22]([OH:28])([CH3:27])[C:23]([F:26])([F:25])[F:24].CCOC(C)=O>CN(C=O)C.[Cu-]=O>[CH3:11][C:12]1[C:17]([Cl:18])=[C:16]([S:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:15]=[CH:14][C:13]=1[NH:20][C:21](=[O:29])[C@:22]([OH:28])([CH3:27])[C:23]([F:26])([F:24])[F:25]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 957384-Mercaptobenzoic acidHCID 69824086HCID 69824086, compound

Product 1

HCID 69883377HCID 69883377, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

4-Mercaptobenzoic acid (308 mg) was added to a suspension of Copper(I) oxide (93 mg) and (R)-N-(2-methyl-3-chloro-4-iodo-phenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 46) (530 mg) in DMF (5 ml). The mixture was heated under Argon to 150° C. for 4.5 hours. The mixture was allowed to cool to ambient temperature and EtOAc (100 ml) was added and the resulting suspension was filtered through diatomaceous earth, and volatile material was removed by evaporation. The residue was purified by chromatography, eluting with 5-10% MeOH in DCM to give the title compound (504 mg). NMR: 1.58 (s, 3H), 2.26 (s, 3H), 7.34 (m, 4H), 7.51 (brs, 1H), 7.92 (brs, 2H), 9.94 (s, 1H), 13.00 (brs, 1H); m/z 432.

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationthe resulting suspension was filtered through diatomaceous earth, and volatile material
  3. customwas removed by evaporation
  4. customThe residue was purified by chromatography
  5. washeluting with 5-10% MeOH in DCM

Sources & evidence

ORD record
ord-3fe7bba0ea1e478f9481203abd573099
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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