Trifluoroacetic acid → (5S)-3-[3-fluoro-4-[4-(hydroxymethyl)imidazol-1-yl]phenyl]-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-one

HRID 8148

Reaction equation

HRID 8148 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]([C:28]4[CH:32]=[CH:31][O:30][N:29]=4)C(OC(C)(C)C)=O)[O:16][C:15]3=[O:33])=[CH:10][C:9]=2[F:34])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[O:30]1[CH:31]=[CH:32][C:28]([NH:20][CH2:19][C@@H:17]2[O:16][C:15](=[O:33])[N:14]([C:11]3[CH:12]=[CH:13][C:8]([N:6]4[CH:7]=[C:3]([CH2:2][OH:1])[N:4]=[CH:5]4)=[C:9]([F:34])[CH:10]=3)[CH2:18]2)=[N:29]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 539752563-(4-(4-Hydroxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

Product 1

HCID 497419(5S)-3-[3-fluoro-4-[4-(hydroxymethyl)imidazol-1-yl]phenyl]-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-oneYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-(4-Hydroxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (360 mg, 0.76 mM) was dissolved in dichloromethane (10 ml) and treated with trifluoroacetic acid (10 ml). After stirring for 30 minutes solvent was evaporated, the residue repeatedly evaporated to dryness with dichloromethane (3×10 ml), and the resulting gum dissolved in water (10 ml). The solution was made basic with concentrated aqueous ammonia, and the resulting precipitate filtered, washed with water and dried to give title product (190 mg).

Workup

  1. customwas evaporated
  2. customthe residue repeatedly evaporated to dryness with dichloromethane (3×10 ml)
  3. dissolutionthe resulting gum dissolved in water (10 ml)
  4. filtrationthe resulting precipitate filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-a0a6c4dccdde4393b6c140e0b62c2cd2
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Linked notes

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