Ethanol → HCID 178467446, compound

HRID 1241341Notes

Reaction equation

HRID 1241341 reaction equation
[H-].[Na+].F[C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[C:6]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([P:33](=[O:36])([OH:35])[OH:34])([OH:32])[PH2:30]=[O:31])=[CH:25][CH:24]=2)[N:5]=1.[CH2:37]([OH:39])[CH3:38]>>[CH2:37]([O:39][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[C:6]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([P:33](=[O:36])([OH:35])[OH:34])([OH:32])[PH2:30]=[O:31])=[CH:25][CH:24]=2)[N:5]=1)[CH3:38]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 24758Sodium hydrideHCID 178527017HCID 178527017, compound

Product 1

HCID 178467446HCID 178467446, compound

Conditions

Temperature
0 °C

Procedure

To a cooled flask (0° C.) under an atmosphere of N2 containing 0.096 g (4.02 mmol) of sodium hydride was added 2.0 mL of absolute ethanol. After the effervescence had ceased, the solution was transferred via pipette to a cooled (0° C.) pressure flask, under an atmosphere of N2, containing a mixture of [(4-{2-Fluoro-9-[2-(3-hydroxy-phenyl)-ethyl]-9H -purin-6-ylamino}-phenyl)-hydroxy-phosphinoylmethyl]-phosphonic acid (0.199 g, 0.39 mmol) in 2.0 mL of absolute ethanol. Upon sealing the reaction vessel, the resulting mixture was stirred at ambient temperature for ˜10 min, then heated at 80° C. overnight. Ethanol was removed via N2 flow (slight heat) and the resulting thick suspension was dissolved in 25 mL of H2O (adjusted to pH ˜8 with 10% NaOH), filtered (0.2 μm, PTFE filter), and purified by RP-HPLC (CH3CN/H2O). Lyophilization provided a white solid (0.105 g): m/z 532 (M−H).

Workup

  1. additionunder an atmosphere of N2, containing
  2. temperatureheated at 80° C. overnight
  3. customEthanol was removed via N2
  4. temperature(slight heat)
  5. dissolutionthe resulting thick suspension was dissolved in 25 mL of H2O (adjusted to pH ˜8 with 10% NaOH)
  6. filtrationfiltered
  7. filtration(0.2 μm, PTFE filter)
  8. custompurified by RP-HPLC (CH3CN/H2O)

Sources & evidence

ORD record
ord-0178faa1a7f3426681a081cf7d17c64c
Source dataset
uspto-grants-2006_10
Patent number
US07115589B2

Reaction notes

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