Trifluoroacetic acid → HCID 16129174, compound

HRID 1047093Notes

Reaction equation

HRID 1047093 reaction equation
[C:1]([C@:3]1([CH2:20][O:21]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=C(OC)C=2OC)[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]1N=[N+]=[N-])#[CH:2].[F:45]C(F)(F)C(O)=O.[OH-].[NH4+]>C(Cl)Cl>[C:1]([C@:3]1([CH2:20][OH:21])[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[F:45])#[CH:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 86650165HCID 86650165, compound

Product 1

HCID 16129174HCID 16129174, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4′-C-ethynyl-5′-O-(dimethoxytrityl)-3′-fluoro-3′-deoxythymidine (12, X═F) (1 mmol) in a solution of 1% trifluoroacetic acid in methylene chloride (20 mL) is stirred at room temperature for 3 h and neutralized with ammonium hydroxide. Solvent is evaporated to dryness under reduced pressure and the residue is purified by silica gel column chromatography (2-5% MeOH in methylene chloride) to give 4′-C-ethynyl-FLT (Ia, X═F).

Workup

  1. customSolvent is evaporated to dryness under reduced pressure
  2. customthe residue is purified by silica gel column chromatography (2-5% MeOH in methylene chloride)
  3. customto give 4′-C-ethynyl-FLT (Ia, X═F)

Sources & evidence

ORD record
ord-ba627f63ffe0465f84a96d37c9ca7b4d
Source dataset
uspto-grants-2013_10
Patent number
US08569478B2

Reaction notes

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