Trifluoroacetic acid → HCID 136110451, compound

HRID 2113948Notes

Reaction equation

HRID 2113948 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 0.1 N NaOH aqueous solution (6.3 ml, 0.63 mmole) at room temperature. At intervals, an aliquot was taken and neutralized with 0.5 N trifluoroacetic acid. The aliquots were evaporated and analyzed by HPLC to monitor the progress of the reaction. After 4 hours, 0.5 N 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-31a23e3e8b404c54810a2874747e8bc7
Source dataset
uspto-grants-2008_10
Patent number
US07432274B2

Reaction notes

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