Trifluoroacetic acid → HCID 58280157, compound

HRID 2189118Notes

Reaction equation

HRID 2189118 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@@H:11]([O:14][C:15]2[C:16]3[C:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH2:10][C@H:9]1[CH2:38][CH2:39][C:40]([OH:42])=[O:41])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([C:23]2[C:16]3[C:15]([O:14][C@@H:11]4[CH2:12][CH2:13][NH:8][C@H:9]([CH2:38][CH2:39][C:40]([OH:42])=[O:41])[CH2:10]4)=[N:20][CH:19]=[N:18][C:17]=3[O:21][C:22]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58280270HCID 58280270, compound

Product 1

HCID 58280157HCID 58280157, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir 34 mg of 3-[(2R,4R)-1-(tert-butoxycarbonyl)-4-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}piperidin-2-yl]propanoic acid in approx. 0.1 ml of a 3:2 mixture of trifluoroacetic acid and dichloromethane at RT for 30 min. Then remove the volatile components under reduced pressure and dry the residue under high vacuum. Take up the residue in acetonitrile/water and neutralize with 1N sodium hydroxide solution (pH approx. 7). Filter off the precipitated colourless solid with suction, wash twice with water and twice with acetonitrile and dry under high vacuum. 20 mg (71.3% of theory) of the target compound are obtained.

Workup

  1. customThen remove the volatile components under reduced pressure
  2. customdry the residue under high vacuum
  3. filtrationFilter off the precipitated colourless solid with suction
  4. washwash twice with water and twice with acetonitrile
  5. customdry under high vacuum
  6. custom20 mg (71.3% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-600ed43c96f64d0083268921324d1e46
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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