HCID 13923453, compound → 3'-Azido-2',3'-dideoxy-5-ethyluridine

HRID 1904994Notes

Reaction equation

HRID 1904994 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:7][C@@H:6]([N:30]2[CH:37]=[C:36]([CH2:38][CH3:39])[C:34](=[O:35])[NH:33][C:31]2=[O:32])[CH2:5]1)=[N+:2]=[N-:3]>C(O)(=O)C>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:30]2[CH:37]=[C:36]([CH2:38][CH3:39])[C:34](=[O:35])[NH:33][C:31]2=[O:32])[CH2:5]1)=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 13923453HCID 13923453, compound

Product 1

HCID 4513663'-Azido-2',3'-dideoxy-5-ethyluridineYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3'-azido-5-ethyl-5'-O-trityl-2',3'-dideoxyuridine (0.9 g, 1.72 mmole) and 80% acetic acid (25 ml) is heated at 85°-90° C. for 40 minutes, after which acetic acid is evacuated in vacuo to a solid in which water (50 ml) is added, and the mixture is stirred for 10 minutes. The solution is filtered through a celite pad, and then the filtrate is extracted with n-hexane. The water layer is separated, evaporated down to ca. 2 ml, and then the solution is freeze-dried to yield an amorphous powder (400 mg, 83%). Recrystallization from MeOH gives fine needles. m.p. 118°-120° C.

Workup

  1. temperatureis heated at 85°-90° C. for 40 minutes
  2. customafter which acetic acid is evacuated in vacuo to a solid in which water (50 ml)
  3. additionis added
  4. filtrationThe solution is filtered through a celite pad
  5. extractionthe filtrate is extracted with n-hexane
  6. customThe water layer is separated
  7. customevaporated down to ca. 2 ml
  8. customthe solution is freeze-dried

Sources & evidence

ORD record
ord-8bb199cb2ac5405c87773fb3225a4701
Source dataset
uspto-grants-1989_06
Patent number
US04841039

Reaction notes

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