Formic Acid → HCID 178455376, compound

HRID 1747696Notes

Reaction equation

HRID 1747696 reaction equation
C([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[O:23][C@@H:24]1[CH2:28][C@@H:27]([CH2:29][O:30][Si](C(C)(C)C)(C)C)[C@@H:26]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:25]1)C1C=CC=CC=1.C(O)=O.CO>[Pd]>[Si:39]([O:38][C@H:26]1[CH2:25][C@H:24]([O:23][C:13]2[N:12]=[CH:11][N:10]=[C:9]3[C:14]=2[N:15]=[C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:8]3)[CH2:28][C@H:27]1[CH2:29][OH:30])([C:42]([CH3:43])([CH3:44])[CH3:45])([CH3:40])[CH3:41]

Participants

5

Reactant 3

HCID 284Formic Acid3×HCID 887MethanolHCID 66797688HCID 66797688, compound

Product 1

HCID 178455376HCID 178455376, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst3×

Procedure

A suspension of 9-benzyl-6-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl]oxy}-8-phenyl-9H-purine (0.161 g, 0.000249 mol), 10% Pd/C (0.04 g, 0.00004 mol) and formic acid (0.1 mL, 0.003 mol) in methanol (11.0 mL, 0.272 mol) was stirred under an atmosphere of nitrogen overnight. Added formic acid (0.2 mL, 0.005 mol) and 10% Pd/C (0.04 g, 0.00004 mol) to the reaction and stirred 24 h. Added 10% Pd/C (0.060 g, 0.000056 mol) and formic acid (0.2 mL, 0.005 mol) to the reaction and stirred an additional 24 h. The reaction was purged with nitrogen and filtered the mixture through celite with DCM. The filtrate was concentrated, purified by flash chromatography (30 to 50% ethyl acetate/hexane) to obtain 30 mg (27%). LC/MS: Rt=2.08 min, ES+ 441.18 (AA standard).

Workup

  1. stirringstirred 24 h
  2. customto the reaction
  3. stirringstirred an additional 24 h
  4. customThe reaction was purged with nitrogen
  5. filtrationfiltered the mixture through celite with DCM
  6. concentrationThe filtrate was concentrated
  7. custompurified by flash chromatography (30 to 50% ethyl acetate/hexane)
  8. customto obtain 30 mg (27%)

Sources & evidence

ORD record
ord-f0e354ef9f9a42d0a7850fd4290df5e2
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

Loading…