Trifluoroacetic acid → HCID 136110451, compound

HRID 1383702Notes

Reaction equation

HRID 1383702 reaction equation
N[C@H](C([O:8][CH2:9][CH2:10][C@@H:11]([CH2:24][O:25][C:26](=[O:32])[C@H:27]([CH:29]([CH3:31])[CH3:30])[NH2:28])[CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:22])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2)=O)C(C)C.[OH-].[Na+].FC(F)(F)C(O)=O>>[OH:8][CH2:9][CH2:10][C@@H:11]([CH2:24][O:25][C:26](=[O:32])[C@H:27]([CH:29]([CH3:30])[CH3:31])[NH2:28])[CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:22])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 14798Sodium HydroxideHCID 135829459HCID 135829459, compound

Product 1

HCID 136110451HCID 136110451, compoundYield 13.6%

Procedure

(R)-9-(4-(L-valyloxy)-2-(L-valyloxymethyl)butyl)guanine from Example 23 step b) (100 mg, 0,126 mmole) was dissolved in 0.1N NaOH aqueous solution (6.3 ml, 0.63 mmole) at room temperature. At intervals, an aliquot was taken and neutralized with 0.5N trifluoroacetic acid. The aliquots were evaporated and analyzed by HPLC to monitor the progress of the reaction. After 4 hours, 0.5N trifluoroacetic acid solution (1.26 ml, 0.63 mmole) was added to the solution and the reaction mixture was evaporated. The desired product was purified by HPLC, (YMC, 50×4.6 mm, gradient 0.1% TFA+0-50% 0.1% TFA in acetonitrile, in 20 minutes, UV detection at 254 nm. Yield: 13.6%

Workup

  1. customThe aliquots were evaporated
  2. customthe progress of the reaction
  3. customthe reaction mixture was evaporated
  4. customThe desired product was purified by HPLC
  5. wait(YMC, 50×4.6 mm, gradient 0.1% TFA+0-50% 0.1% TFA in acetonitrile, in 20 minutes

Sources & evidence

ORD record
ord-f34702c55fa6487ab77230960b9af148
Source dataset
uspto-grants-2001_07
Patent number
US06255312B1

Reaction notes

Loading…