Trifluoroacetic acid → HCID 24872067, compound

HRID 1424316Notes

Reaction equation

HRID 1424316 reaction equation
C(O)(C(F)(F)F)=O.[NH:8]1[CH2:11][CH:10]([CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:9]1.C[O:21][C:22](=[O:46])[CH:23]([NH:34][C:35](=[O:45])[C:36]1[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=1[CH3:44])[CH2:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(N(CC)CC)C>ClCCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][CH2:12][CH:10]1[CH2:11][N:8]([C:28]2[CH:29]=[CH:30][C:25]([CH2:24][CH:23]([NH:34][C:35](=[O:45])[C:36]3[C:37]([CH3:44])=[CH:38][C:39]([CH3:43])=[CH:40][C:41]=3[CH3:42])[C:22]([OH:46])=[O:21])=[CH:26][CH:27]=2)[CH2:9]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 57660930HCID 57660930, compoundHCID 69078566HCID 69078566, compound

Product 1

HCID 24872067HCID 24872067, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Procedure

153 mg (0.203 mmol) TFA salt of (10) together with 150 mg (0.406 mmol) 2-(2,4,6-trimethylbenzoylamino)-3-(4-boronophenyl)propionic acid methyl ester (12), 844 μl (6.1 mmol) triethlamine and 74 mg (0.406 mmol) Cu(OAc)2 were stirred in 2.5 ml DCE for 20 min under ultrasonification and then stirring was continued for another 20 h at room temperature. The reaction mixture was filtered over a pad of Celite, the solvent was removed under reduced pressure and the residue was dissolved in acetonitrile to be filtered over another pad of Celtite. After the solvent was removed, the crude methyl ester was dissolved in 9 ml methanol and stirred with 4 ml 0.5 M NaOH over the weekend. Solids were removed by filtration and the reaction mixture was purified by reversed phase HPLC using a water/acetonitrile gradient containing 0.1% TFA yielding the TFA salt of (11) after lyophilization as a white powder.

Workup

  1. filtrationThe reaction mixture was filtered over a pad of Celite
  2. customthe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in acetonitrile
  4. filtrationto be filtered over another pad of Celtite
  5. customAfter the solvent was removed
  6. dissolutionthe crude methyl ester was dissolved in 9 ml methanol
  7. stirringstirred with 4 ml 0.5 M NaOH over the weekend
  8. customSolids were removed by filtration
  9. customthe reaction mixture was purified by reversed phase HPLC
  10. additioncontaining 0.1% TFA yielding the TFA salt of (11) after lyophilization as a white powder

Sources & evidence

ORD record
ord-b3336f78beba49c1b084ea4b5618e4bd
Source dataset
uspto-grants-2015_01
Patent number
US08927534B2

Reaction notes

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