Trifluoroacetic acid → HCID 57835925, compound

HRID 731209Notes

Reaction equation

HRID 731209 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 76.4 (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 76.5 (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 76.5 was separated into two enantiomers 76.6 and 76.7 using chiral preparative AD-H column (8% IPA/92% hexanes). The stereochemistry of 76.6 and 76.7 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-09f341e7711342ad9bf0f611e9801cec
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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