Trifluoroacetic acid → HCID 59238206, compound

HRID 2068585Notes

Reaction equation

HRID 2068585 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]=[C:21]3[C:17]([N:18]([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[CH:19]=[N:20]3)=[C:16]([NH2:31])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.[C:32]([C:36](O)=O)(F)(F)F.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+].[CH2:50]1[CH2:54]O[CH2:52][CH2:51]1>C(Cl)Cl>[CH:50]1[C:54]2[CH:36]([CH2:32][O:5][C:6]([N:8]3[CH2:9][CH2:10][N:11]([C:14]4[N:22]=[C:21]5[C:17]([N:18]([CH2:23][C:24]([OH:26])=[O:25])[CH:19]=[N:20]5)=[C:16]([NH2:31])[N:15]=4)[CH2:12][CH2:13]3)=[O:7])[C:52]3[C:51](=[CH:52][CH:54]=[CH:50][CH:51]=3)[C:50]=2[CH:54]=[CH:52][CH:51]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 67211772HCID 67211772, compound

Product 1

HCID 59238206HCID 59238206, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of crude 4 (7 g) in CH2Cl2 (200 ml) was gradually added CF3CO2H (200 ml). The mixture was stirred overnight. Then potassium carbonate was added to adjust the pH to 7.5. Saturated aqueous sodium bicarbonate solution was then added to keep the pH 8-9. After the adjustment of the pH, Fmoc-OSuc (10 g) in THF was added to the mixture and it was stirred for further 5 hours. THF was evaporated and the mixture was washed with ethyl acetate (150 ml×2). The water layer was tuned the pH to 3 with 2N HCl and then extracted with dichloromethane (150 ml×7). The organic layer was dried over Na2SO4 and concentrated to give the crude product (0.5 g). Further purification by preparative HPLC afforded 4-(6-amino-7-carboxymethyl-7H-purin-2-yl)-piperazine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester, 6 (50 mg).

Workup

  1. stirringwas stirred for further 5 hours
  2. customTHF was evaporated
  3. washthe mixture was washed with ethyl acetate (150 ml×2)
  4. extractionextracted with dichloromethane (150 ml×7)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customto give the crude product (0.5 g)
  8. customFurther purification by preparative HPLC

Sources & evidence

ORD record
ord-6dd2a4433b0e4bc08d629e901fcac725
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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