Trifluoroacetic acid → HCID 67105651, compound

HRID 885274Notes

Reaction equation

HRID 885274 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16](=[O:29])[NH:17][C@@H:18]([CH3:28])[C:19]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[SiH](C)C1C=CC=CC=1.[OH-].[K+]>CCOC(C)=O.[Cl-].[Na+].O.C1COCC1>[CH2:8]([O:15][C:16](=[O:29])[NH:17][C@@H:18]([CH3:28])[CH:19]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[OH:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 13014DimethylphenylsilaneHCID 14797Potassium HydroxideHCID 67105892HCID 67105892, compound

Product 1

HCID 67105651HCID 67105651, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (2 mL) was cooled to −5° C. [(S)-2-(4-Chloro-phenyl)-1-methyl-2-oxo-ethyl]-carbamic acid benzyl ester (0.87 g, 2.7 mmol) was added slowly, followed by dimethylphenylsilane (0.5 mL, 3.3 mmol), and the mixture was stirred for 4 hours. Once no starting material was seen by analytical tlc, the mixture was cooled to 0° C. and treated with 50% aqueous KOH (10 mL), followed by THF. After stirring at mom temperature for 5 hours, only starting material was seen by analytical tlc, and so the solution was diluted with EtOAc and brine. The organic layer was separated and concentrated, and the crude material was purified to give the desired product.

Workup

  1. additionwas added slowly
  2. stirringAfter stirring at mom temperature for 5 hours
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customthe crude material was purified

Sources & evidence

ORD record
ord-5af0e067acc540d1b89b9da6ff9b086b
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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