Water → HCID 18455981, compound

HRID 1272110Notes

Reaction equation

HRID 1272110 reaction equation
C(OC([C:6]1[N:16]([CH:17]([CH3:27])[CH2:18][NH:19][C:20](OC(C)(C)C)=[O:21])[C:9]2=[N:10][C:11]([Cl:15])=[C:12]([CH3:14])[CH:13]=[C:8]2[CH:7]=1)=O)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+].O>ClCCl.C(OCC)(=O)C>[Cl:15][C:11]1[N:10]=[C:9]2[C:8](=[CH:13][C:12]=1[CH3:14])[CH:7]=[C:6]1[N:16]2[CH:17]([CH3:27])[CH2:18][NH:19][C:20]1=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 86596348HCID 86596348, compound

Product 1

HCID 18455981HCID 18455981, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of 0.50 g (1.25 mmol) ®-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-6-chloro-5-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester in 6 mL dichloromethane was added 1.91 mL (2.85 g, 25.0 mmol) trifluoroacetic acid; the ice-bath was removed after complete addition. After 45 min., the volatile components were removed and the residue was dissolved in 3 mL methanol then treated cautiously with 0.70 g (5.0 mmol) potassium carbonate. After 2 h the reaction mixture was poured into water and ethyl acetate and the separated aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated. The residue was dissolved in dichloromethane and tert-butyl methyl ether, evaporated under vacuum until a suspension appeared, then cooled to 0° C. The ice-cold suspension was filtered and the filter cake was washed with tert-butyl methyl ether to give the product as a colourless solid (73.7%).

Workup

  1. customthe ice-bath was removed
  2. additionafter complete addition
  3. customthe volatile components were removed
  4. dissolutionthe residue was dissolved in 3 mL methanol
  5. extractionthe separated aqueous phase was extracted twice with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. dissolutionThe residue was dissolved in dichloromethane
  10. customtert-butyl methyl ether, evaporated under vacuum until a suspension
  11. filtrationThe ice-cold suspension was filtered
  12. washthe filter cake was washed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-301d09a7ffd64684862900d51cf902d9
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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