Trifluoroacetic acid → HCID 57835925, compound

HRID 1675285Notes

Reaction equation

HRID 1675285 reaction equation
C(O)(C(F)(F)F)=O.COC1C=CC(C[O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([C:36]3[CH:40]=[CH:39][O:38][N:37]=3)[CH2:23][C:24]([O:26][CH2:27][C:28]3C=CC(OC)=CC=3)=[O:25])=[CH:18][CH:17]=2)=CC=1>C(Cl)Cl>[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:36]2[CH:40]=[CH:39][O:38][N:37]=2)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57835887HCID 57835887, compound

Product 1

HCID 57835925HCID 57835925, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) was added to 40.4 (940 mg) in DCM (10 mL). The mixture was stirred at room temperature for 1.5 hours. TFA and DCM were removed under vacuum, and the residue was treated with EtOH (50 mL). The insoluble solid was removed by filtration. To the filtrate was added concentrated sulfuric acid (2 drops). The mixture was stirred at 80° C. overnight. After concentration, the crude product was purified by flash chromatography to give 40.5 (410 mg). MS ESI (pos.) m/e: 262 (M+H). 1HNMR (CDCl3) δ 8.29 (d, 1H), 7.12 (d, 2H), 6.76 (d, 2H), 6.10 (d, 1H), 4.56 (t, 1H), 4.10 (q, 2H), 3.27 (dd, 1H), 2.97 (dd, 1H), 1.19 (t, 3H). The racemic compound 40.5 was separated into two enantiomers 40.6 and 40.7 using chiral preparative AD-H column (8% IPA/92% hexanes). The stereochemistry of 40.6 and 40.7 was assigned arbitrarily.

Workup

  1. customTFA and DCM were removed under vacuum
  2. additionthe residue was treated with EtOH (50 mL)
  3. customThe insoluble solid was removed by filtration
  4. additionTo the filtrate was added concentrated sulfuric acid (2 drops)
  5. stirringThe mixture was stirred at 80° C. overnight
  6. concentrationAfter concentration
  7. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-0507b6a5aba24b5ca81834602a5a0c41
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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