Acetic Anhydride → 1-(3-O-acetyl-2,5-dideoxy-5-iodo-beta-D-threopentofuranosyl)thymine

HRID 1181912Notes

Reaction equation

HRID 1181912 reaction equation
[I:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@H:4]1[OH:17].[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:17][C@H:4]1[C@@H:3]([CH2:2][I:1])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5]1)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 128500761-(2,5-dideoxy-5-iodo-beta-D-threo-pentofuranosyl)thymine

Product 1

HCID 121116121-(3-O-acetyl-2,5-dideoxy-5-iodo-beta-D-threopentofuranosyl)thymineYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 1-(2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine (for preparation see ref. J. Org. Chem. 1964, 29, 2076) (5.1 g, 14.5 mmol) in anhydrous pyridine (50 mL) at 0° C. under argon was added acetic anhydride (7.0 ml, 75.4 mmol). The reaction mixture was stirred at room temperature for 17 h. The reaction mixture was cooled with ice bath and quenched by slow addition of water (15 mL). The reaction mixture was stirred for 30 min and concentrated to dryness, and co-evaporated with anhydrous toluene three times. The residue was re-dissolved in dichloromethane and chromatographed on silica gel with 1-3% methanol in ethyl acetate gave 4.4 g of 1-(3-O-acetyl-2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine (49).

Workup

  1. temperatureThe reaction mixture was cooled with ice bath
  2. customquenched by slow addition of water (15 mL)
  3. stirringThe reaction mixture was stirred for 30 min
  4. concentrationconcentrated to dryness
  5. dissolutionThe residue was re-dissolved in dichloromethane
  6. customchromatographed on silica gel with 1-3% methanol in ethyl acetate

Sources & evidence

ORD record
ord-ab701c16beda478e803e1f513f351e98
Source dataset
uspto-grants-2007_10
Patent number
US07285658B2

Reaction notes

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