Trifluoroacetic acid → HCID 86699098, compound

HRID 1424180Notes

Reaction equation

HRID 1424180 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][N:17]2[CH:26]=1)[C@@H:9]([CH3:13])[C:10]([NH2:12])=[O:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@H:8]([C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][N:17]2[CH:26]=1)[C@@H:9]([CH3:13])[C:10]([NH2:12])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86699115HCID 86699115, compound

Product 1

HCID 86699098HCID 86699098, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl((1S,2R)-3-amino-1-(6-(tert-butyl)imidazo[1,2-a]pyridin-2-yl)-2-methyl-3-oxopropyl)carbamate (Preparation 37, 311 mg) was dissolved in dichloromethane (ca 4 mL) and excess trifluoroacetic acid (ca 0.5 mL) was added. The reaction mixture was stirred for 18 hours then the solvent was removed in vacuo. The residue was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The product stayed in the aqueous phase. The aqueous phase was adjusted to pH=10 with 1N sodium hydroxide, then sodium chloride was added until the solution was saturated. The aqueous phase was extracted three times with ethyl acetate. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by silica gel column chromatography eluting with 0-100% CMA80 in dichloromethane to afford 233 mg of the title compound as a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated aqueous sodium bicarbonate
  4. additionsodium chloride was added until the solution
  5. extractionThe aqueous phase was extracted three times with ethyl acetate
  6. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by silica gel column chromatography
  10. washeluting with 0-100%

Sources & evidence

ORD record
ord-63665a8283ac45f3a5afd9e6f92e1ac8
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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