Trifluoroacetic acid → HCID 136110451, compound

HRID 1166708Notes

Reaction equation

HRID 1166708 reaction equation
[NH2:1][C@H:2]([C:6]([O:8][CH2:9][C@H:10]([CH2:23][CH2:24][O:25]C(=O)[C@H](C(C)C)N)[CH2:11][N:12]1[CH:20]=[N:19][C:18]2[C:17](=[O:21])[NH:16][C:15]([NH2:22])=[N:14][C:13]1=2)=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].FC(F)(F)C(O)=O>>[OH:25][CH2:24][CH2:23][C@@H:10]([CH2:9][O:8][C:6](=[O:7])[C@H:2]([CH:3]([CH3:4])[CH3:5])[NH2:1])[CH2:11][N:12]1[CH:20]=[N:19][C:18]2[C:17](=[O:21])[NH:16][C:15]([NH2:22])=[N:14][C:13]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-c36ec8755dfb4a2c9ec1915c6cac69e5
Source dataset
uspto-grants-2003_09
Patent number
US06613936B1

Reaction notes

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