Trifluoroacetic acid → HCID 86593734, compound

HRID 272101Notes

Reaction equation

HRID 272101 reaction equation
C([O:4][CH:5]1[C:10]([OH:14])([CH2:11][CH2:12][CH3:13])[CH:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:8]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:7]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]1[O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)C=C.C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O>C(O)C>[CH2:16]([O:15][CH:9]1[CH:8]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:7]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:6]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:5]([OH:4])[C:10]1([OH:14])[CH2:11][CH2:12][CH3:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 86593735HCID 86593735, compound

Product 1

HCID 86593734HCID 86593734, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 (0.30 g, 0.48 mmol) was dissolved in 20 mL aqueous ethanol (90%). 93 mg (0.101 mmol) Wilkinson catalyst and 50 μL diisopropylethyl amine were added and the mixture was heated to reflux for 12 hours. After cooling to room temperature 30 μL triflouro acetic acid was added and the solution was allowed to stir for 12 days by when the starting material had disappeared. The solution was dried in high vacuum and the residue was dissolved in t-butylmethyl ether and washed with 0.5 M phosphate buffer pH=7 and brine. The organic phase was filtered after being dried over Na2SO4 and the filtrate was dried under reduced pressure. Further purification was accomplished by preparative HPLC (89% MeOH, 40 m/min, tRet=21.40 min) to give 220 mg of 21 (0.38 mmol, 78.4% yield) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 12 hours
  3. additionwas added
  4. customThe solution was dried in high vacuum
  5. dissolutionthe residue was dissolved in t-butylmethyl ether
  6. washwashed with 0.5 M phosphate buffer pH=7 and brine
  7. filtrationThe organic phase was filtered
  8. dry with materialafter being dried over Na2SO4
  9. customthe filtrate was dried under reduced pressure
  10. customFurther purification
  11. customwas accomplished by preparative HPLC (89% MeOH, 40 m/min, tRet=21.40 min)

Sources & evidence

ORD record
ord-79597f1c528949c3b7059e0d736671c7
Source dataset
uspto-grants-2008_11
Patent number
US07453006B2

Reaction notes

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