Hydrochloric Acid → HCID 22313821, compound

HRID 965975Notes

Reaction equation

HRID 965975 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, dried_over MgSO4
  3. concentrationconcentrated in vacuo
  4. customthe residue was used for next reaction without further purification

Sources & evidence

ORD record
ord-ee12c62663064beca03bd6226a651640
Source dataset
uspto-grants-2005_10
Patent number
US06951876B2

Reaction notes

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