Glycerol → HCID 11782182, compound

HRID 366842Notes

Reaction equation

HRID 366842 reaction equation
[CH2:1](Br)[C:2]#[CH:3].N12CCCN=C1CCCCC2.[CH3:16][O:17][C@@H:18]1[C@H:22]([OH:23])[C@@H:21]([CH2:24][OH:25])[O:20][C@H:19]1[N:26]1[C:35]2[N:34]=[CH:33][N:32]=[C:30]([OH:31])[C:29]=2[N:28]=[CH:27]1.OCC(CO)O>CC(N(C)C)=O.CO>[CH3:16][O:17][C@@H:18]1[C@H:22]([OH:23])[C@@H:21]([CH2:24][OH:25])[O:20][C@H:19]1[N:26]1[C:35]2[N:34]=[CH:33][N:32]([CH2:3][C:2]#[CH:1])[C:30](=[O:31])[C:29]=2[N:28]=[CH:27]1

Participants

7

Reactant 4

HCID 753GlycerolHCID 7842Propargyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 178496714HCID 178496714, compound

Product 1

HCID 11782182HCID 11782182, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

Propargyl bromide (2.2 ml, 19.7 mmol) and 1,8 diazabicyclo[5.4.0]undec-7-ene (DBU) (2.7 ml, 17.7 mmol) were added to a suspension of 2'-O-methylinosine (5.4 g, 19.0 mmol) in dimethylacetamide (100 ml). The reaction mixture was stirred at room temperature under argon for 18 hours at which time an additional 1 ml of DBU was added. After 6 hours, the reaction solution was evaporated in vacuo to an oil and dried onto 20 g of silica gel. Pure product was isolated by silica gel chromatography with a 2-5% gradient of methanol in chloroform. FABMS (glycerol & methanol) m/z 321 (MH+). 1H-NMR (DMSO-d6): 8.50 (1H,s, H2); 8.41 (1H, s, H8); 5.96 (1H, d, H1'); 5.28 (1H, d, 2'--OH); 5.09 (1H, t, 5'--OH); 4.82 (2H, s, CH2); 4.27 (2H, m, H2', H3'); 3.94 (1H, m, H4'); 3.60 (2H, m, H5', H5"); 3.41 (1H, s, CH).

Workup

  1. additionwas added
  2. customthe reaction solution was evaporated in vacuo to an oil
  3. customdried onto 20 g of silica gel
  4. customPure product was isolated by silica gel chromatography with a 2-5% gradient of methanol in chloroform

Sources & evidence

ORD record
ord-057d43a8f5a94c02aa947e1c1e859ae3
Source dataset
uspto-grants-2000_10
Patent number
US06130324

Reaction notes

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