Hydrochloric Acid → HCID 22313821, compound

HRID 394886Notes

Reaction equation

HRID 394886 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[CH3:13][C:14]1[CH:15]=[C:16]([C:25](=[O:27])[CH3:26])[CH:17]=[CH:18][C:19]=1[C:20]1[N:21]=[CH:22][S:23][CH:24]=1.Cl>COC(C)(C)C>[F:9][C:2]([F:1])([F:8])[C:3](=[O:5])[CH2:26][C:25]([C:16]1[CH:17]=[CH:18][C:19]([C:20]2[N:21]=[CH:22][S:23][CH:24]=2)=[C:14]([CH3:13])[CH:15]=1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 22313835HCID 22313835, compound

Product 1

HCID 22313821HCID 22313821, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a stirred solution of ethyl trifluoroacetate (500 mg, 3.52 mmol) in tert-butyl methyl ether (4 ml) was added sodium methoxide (28 wt.% solution in methanol; 0.9 ml, 4.0 mmol) over 2 min. A solution of 1-[3-methyl-4-(1,3-thiazol-4-yl)phenyl]-1-ethanone from step 4 (714 mg, 3.33 mmol) in t-butylmethylether (6 ml) was added dropwise over 5 minutes, and the mixture was stirred for 20 hours. 2N HCl (10 ml) was added, and the whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo, and the residue was used for next reaction without further purification. (1.05 g, 99% yield).

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customthe residue was used for next reaction without further purification

Sources & evidence

ORD record
ord-2251f20d6152453481d0909ce72c382f
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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