Acetone → 4-(2-Hexanon-1-yl)-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

HRID 1107650Notes

Reaction equation

HRID 1107650 reaction equation
[C:1]([C:7]1[CH:12]=[CH:11][N:10]([C@@H:13]2[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:45])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:24]([O:25][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:14]2[O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9](=[O:46])[N:8]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].CC(C)=[O:49]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.O.ClCCl.[Hg](OC(C)=O)OC(C)=O>[CH2:1]([C:7]1[CH:12]=[CH:11][N:10]([C@@H:13]2[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:45])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:24]([O:25][C:26](=[O:33])[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C@H:14]2[O:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:9](=[O:46])[N:8]=1)[C:2](=[O:49])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 180AcetoneHCID 103941024-(1-Hexyn-1-yl)-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

Product 1

HCID 867554054-(2-Hexanon-1-yl)-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

Reagents, catalysts & solvents 3

HCID 16683746DiacetyloxymercuryCatalystHCID 6344DichloromethaneSolventHCID 131721792acetic H2OSolvent

Procedure

A solution of 14a (0.77 g, 1.2 mmol) in 50 mL acetone is treated with a 0.1M solution of Hg(OAc)2 (15 mL) in aqueous acetic-H2O (1:1) and the mixture stirred at room temperature for 18 hr. The reaction is further diluted with dichloromethane (100 mL), washed with cold saturated NaHCO3 solution, dried over magnesium sulfate and evaporated in vacuo. The resulting residue is flash-chromatographed using chloroform/acetone 19:1 to afford a yellowish solid. This solid is triturated with cold methanol to afford 15a, 0.47 g, 59%. 1H-NMR (DMSO-d6): 12.5 (s, 1 H, enol); 8.0-7.4 (m, 16 H, H-6 plus aromatic); 6.15 (d, 1 H, H-1', J=2 Hz); 5.90 (m, 3 H, H-5, 2',3'); 5.39 (s, 1 H, vinylic, Jvinyl, allyl =<1 Hz)); 2.30, 1.47, 1.24 and 0.86 (4 m, 9 H, n-butyl) . Anal. Calcd for C36H34N2O9 : C, 67.70; H, 5.37; N, 4.39. Found: C, 67.51; H, 5.28; N, 4.28.

Workup

  1. washwashed with cold saturated NaHCO3 solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe resulting residue is flash-chromatographed
  5. customto afford a yellowish solid
  6. customThis solid is triturated with cold methanol

Sources & evidence

ORD record
ord-48ea0305362643d6a8d2408c43c05f19
Source dataset
uspto-grants-2000_05
Patent number
US06060592

Reaction notes

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