Trifluoroacetic acid → HCID 11294723, compound

HRID 1513985Notes

Reaction equation

HRID 1513985 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][C:19]=1[F:20])[C:16]1[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([OH:21])[CH:10]=[CH:9]3)[C:6](OC)([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:24][CH:23]=1)[O:5]2.C(N(CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][C:19]=1[F:20])[C:16]1[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([OH:21])[CH:10]=[CH:9]3)[CH:6]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)=[CH:26][CH:27]=1)[O:5]2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 57552549HCID 57552549, compound

Product 1

HCID 11294723HCID 11294723, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 8,9-Difluoro-5-methoxy-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol (1.1 gm, 21. mmoles) in 30 ml of methylene chloride and add 2 ml of triethylamine and 2 ml of trifluoroacetic acid. Stir at room temperature for 1 hour, neutralize with sodium bicarbonate solution and separate the organic layer. Wash the water layer with methylene chloride and combine the organic layers. Dry the liquid over sodium sulfate and remove the solvent. Purify as described in Preparation 17 to obtain an 18% yield of the racemic. Obtain the individual enantiomers by chiral chromatography using a Chiralpak AD column eluting with ethanol containing 0.2% dimethylethylamine and monitoring at 225 nm.

Workup

  1. customseparate the organic layer
  2. washWash the water layer with methylene chloride
  3. dry with materialDry the liquid over sodium sulfate
  4. customremove the solvent
  5. customPurify
  6. customas described in Preparation 17
  7. customto obtain an 18% yield of the racemic
  8. customObtain the individual enantiomers by chiral chromatography
  9. washeluting with ethanol containing 0.2% dimethylethylamine and monitoring at 225 nm

Sources & evidence

ORD record
ord-53ff8196121446988c1944cbe6aba755
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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