Trifluoroacetic acid → Trifluoroacetic acid

HRID 536649Notes

Reaction equation

HRID 536649 reaction equation
C(OC)(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:22]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)=O.[CH3:33][CH:34]1[O:39][CH:38]([CH3:40])[CH2:37][NH:36][CH2:35]1.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]>CN(C)C=O.C(O)(=O)C>[CH3:40][CH:38]1[O:39][CH:34]([CH3:33])[CH2:35][N:36]([CH2:22][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)[CH2:37]1.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 120884-Formylbenzoic acidHCID 1108622,6-DimethylmorpholineHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 6422Trifluoroacetic acidHCID 16774820HCID 16774820, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Acetic acid (0.34 mL), trimethyl orthoformate (0.66 mL), and sodium triacetoxyborohydride (0.53 g) are successively added to 4-formyl-benzoic acid (150 mg) and 2,6-dimethyl-morpholine (115 mg) dissolved in dimethylformamide (3 mL). The solution is stirred at room temperature overnight. Trifluoroacetic acid (50% in water) is added, the solution is stirred for another 2 h and then concentrated under reduced pressure. The residue is purified by HPLC on reversed phase (MeCN/H2O) to give the title compound as its trifluoroacetic acid salt.

Workup

  1. stirringthe solution is stirred for another 2 h
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by HPLC on reversed phase (MeCN/H2O)

Sources & evidence

ORD record
ord-7772a1cb19a34bfb9a76fcec3d84073f
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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