5'-O-(4,4'-Dimethoxytrityl)thymidine → 3'-O-[(6-nitroveratryl)oxycarbonyl]thymidine

HRID 354216

Reaction equation

HRID 354216 reaction equation
COC1C=CC(C([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26][C@@H:25]2[OH:38])(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1.[Cl-].C[N+]1C=CN([C:48]([O:50][CH2:51][C:52]2[C:61]([N+:62]([O-:64])=[O:63])=[CH:60][C:57]([O:58][CH3:59])=[C:54]([O:55][CH3:56])[CH:53]=2)=[O:49])C=1>ClCCl.N1C=CC=CC=1>[N+:62]([C:61]1[C:52]([CH2:51][O:50][C:48]([O:38][C@@H:25]2[C@@H:24]([CH2:23][OH:22])[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26]2)=[O:49])=[CH:53][C:54]([O:55][CH3:56])=[C:57]([O:58][CH3:59])[CH:60]=1)([O-:64])=[O:63]

Participants

5

Reactant 2

HCID 1624195'-O-(4,4'-Dimethoxytrityl)thymidineHCID 86759466N-methyl-N3-[(6-nitroveratryl)oxycarbonyl]imidazoliumchloride

Product 1

HCID 183459313'-O-[(6-nitroveratryl)oxycarbonyl]thymidineYield 66%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

A solution of 1.97 g 5′-O-(4,4′-dimethoxytrityl)thymidine (3.62 mmol) in 18 ml absolute dichloromethane and 2 ml absolute pyridine is added in a nitrogen atomsphere and in the absence of light to an N-methyl-N3-[(6-nitroveratryl)oxycarbonyl]imidazoliumchloride acylation reaction (19) (produced from 7.25 mmol chloroformic acid-6-nitroveratryl ester). The reaction mixture is stirred in the dark at 4° C. overnight. The molecular sieve is separated and the organic phase is extracted twice against saturated NaHCO3 (100 ml). After drying via Na2SO4, 200 ml of a 10% trichloroacetic acid in dichloroethane are added to the organic phase and stirred at room temperature for 5 minutes. The deep-red solution is extracted twice with saturated NaHCO3 (200 ml), the organic phase is dried via Na2SO4 and evaporated. Purification via flash chromatography (66-80% ethyl acetate in toluene) yielded 1.153 g of the title compound (66% yield)

Workup

  1. customThe molecular sieve is separated
  2. extractionthe organic phase is extracted twice against saturated NaHCO3 (100 ml)
  3. dry with materialAfter drying via Na2SO4, 200 ml of a 10% trichloroacetic acid in dichloroethane
  4. additionare added to the organic phase
  5. stirringstirred at room temperature for 5 minutes
  6. extractionThe deep-red solution is extracted twice with saturated NaHCO3 (200 ml)
  7. dry with materialthe organic phase is dried via Na2SO4
  8. customevaporated
  9. customPurification via flash chromatography (66-80% ethyl acetate in toluene)

Sources & evidence

ORD record
ord-7e2405a62dce4582a7a940684ff7fe7a
Source dataset
uspto-grants-2004_06
Patent number
US06756492B1

Linked notes

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