Potassium sodium tartarate → HCID 52920495, compound

HRID 1842844Notes

Reaction equation

HRID 1842844 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:19][CH2:20][C@@H:21]1[C@@H:25]([O:26]C(=O)C2C=CC=CC=2)[C@H:24]([F:35])[C@H:23]([N:36]2[CH:44]=[N:43][C:42]3[C:37]2=[N:38][CH:39]=[N:40][C:41]=3[NH2:45])[C:22]1=[CH2:46])(=O)C1C=CC=CC=1.[C:47]([CH:50]([CH:52]([C:54]([O-:56])=O)[OH:53])[OH:51])([O-])=[O:48].[Na+].[K+]>C(Cl)Cl.C(O)(C)C.C(Cl)(Cl)Cl>[C@@H:23]1([N:36]2[C:37]3[N:38]=[CH:39][N:40]=[C:41]([NH2:45])[C:42]=3[N:43]=[CH:44]2)[O:53][C@H:52]([CH2:54][OH:56])[C@@H:50]([OH:51])[C@H:47]1[OH:48].[NH2:45][C:41]1[N:40]=[CH:39][N:38]=[C:37]2[C:42]=1[N:43]=[CH:44][N:36]2[C@@H:23]1[C:22](=[CH2:46])[C@H:21]([CH2:20][OH:19])[C@@H:25]([OH:26])[C@@H:24]1[F:35]

Participants

7

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 67432952HCID 67432952, compound

Product 2

HCID 60961AdenosineHCID 52920495HCID 52920495, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Diisobutylaluminum hydride (DIBAL-H, 1.6 mL, 1.0 M in toluene) was added slowly into the solution of compound 14 (160.0 mg, 0.33 mmol) in anhydrous CH2Cl2 at −78° C. After 30 min at the same temperature, the reaction was diluted with isopropyl alcohol/chloroform (4:1) co-solvent (30 mL) and saturated potassium sodium tartrate solution (10 mL) was added. The mixture was stirred at room temperature for 2 h and the organic layer was colleted. The aqueous layer was extracted with isopropyl alcohol/chloroform (4:1) co-solvent (3×10 mL) and organic layer were combined, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on a silica gel (MeOH:CH2Cl2=1:20 to 1:10) to give adenosine analogue 15 (70.0 mg, 76%) as a white solid. mp: 215-218° C. (dec.) [α]25D +151.80° (c 0.23, CHCl3) UV (H2O) λmax 259.0 nm (ε 13998, pH 2), 260.0 nm (e 15590, pH 7), 260.0 nm (ε 15579, pH 11); 1H NMR (400 MHz, CDCl3) δ 8.22 (s, 1H), 8.06 (d, J=2.4 Hz, 1H), 5.86 (dd, J=2.4 and 25.6 Hz, 1H), 5.42 (t, J=2.4 Hz, 1H), 4.93 (td, J=3.2 and 52.4 Hz, 1H), 4.92 (s, 1H, partially buried inside the H2O peak), 4.40 (td, J=3.2 and 10.8 Hz, 1H), 3.88-3.76 (m, 2H), 2.78 (m, 1H); 13C NMR (100 MHz, CDCla) δ 156.0, 152.5, 149.9, 146.1 (d, J=1.0 Hz), 141.1 (d, J=5.2 Hz), 117.9, 111.8, 95.9 (d, J=186.0 Hz), 72.9 (d, J=22.9 Hz), 61.8 (d, J=3.4 Hz), 57.6 (d, J=17.2 Hz), 51.1. Anal. Calcd. for C12H14FN5O2: C, 51.61; H, 5.05; N, 25.08. Found: C, 51.74; H, 5.09; N, 24.92.

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with isopropyl alcohol/chloroform (4:1) co-solvent (3×10 mL) and organic layer
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by column chromatography on a silica gel (MeOH:CH2Cl2=1:20 to 1:10)

Sources & evidence

ORD record
ord-ce57e7493b024be3a2e047fd10a20420
Source dataset
uspto-grants-2015_02
Patent number
US08946244B2

Reaction notes

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