Acetic Acid → HCID 22475621, compound

HRID 2184070Notes

Reaction equation

HRID 2184070 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[C:18]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:19][C:20]([CH3:22])=[O:21].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[OH2:17].[C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])=[O:21].[F:16][C:13]([F:14])([F:15])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH:20]([CH3:22])[CH2:19][C:18]([O:24][CH2:25][CH3:26])=[O:23])=[CH:7][CH:6]=1)([OH:17])[C:9]([F:10])([F:11])[F:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 5003444Sodium cyanoborohydride

Product 2

HCID 22392675Trifluoroacetic acid waterHCID 22475621HCID 22475621, compoundYield 186.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from step 1 (500 mg, 1.9 mmol) and ethyl acetoacetate (0.27 mL, 2.1 mmol) were combined and dissolved in methanol (10 mL) at ambient temperature. To this solution was added glacial acetic acid (0.13 mL, 2.1 mmol) followed by sodium cyanoborohydride (194 mg, 3.1 mmol). After stirring 18 h, the solution was concentrated in vacuo and the resultant oil dissolved in ethyl acetate. The organics were washed with brine, dried over MgSO4, and concentrated. Purification by reverse phase HPLC using a gradient elution of 60:40 H2O/TFA:CH3CN to 0:100 H2O/TFA:CH3CN at 254 nm afforded the title compound as a white solid (440 mg, 61%): mp=103° C.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionthe resultant oil dissolved in ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by reverse phase HPLC
  7. washa gradient elution of 60:40 H2O/TFA

Sources & evidence

ORD record
ord-6bbee98a2414413d9016e027f355f1dd
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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