Reaction #4985

ord-f862215dba7846cf8cae5bec600dc198

Reaction equation

O=c1ccn([C@]2(I)O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1
Iodouridine
C#CCNC(=O)C(F)(F)F
N-propargyltrifluoroacetamide
CO
methanol
→
O=C(NCC#Cc1cn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]c1=O)C(F)(F)F
alkynylamino nucleoside
O=C(NCC#Cc1cn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]c1=O)C(F)(F)F
5-(3-trifluoroacetamido-1-propynyl)-2', 3'-dideoxyuridine

Reactants

O=c1ccn([C@]2(I)O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1
Iodouridine
C#CCNC(=O)C(F)(F)F
N-propargyltrifluoroacetamide
CO
methanol

Reagents

None

Solvents

ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto dry
  2. 2
    Othervacuum-drying

Procedure

Iodouridine 21 was coupled for 3 hours to N-propargyltrifluoroacetamide following the general method given in Example 5C. Chromatography with a 0-5% methanol in dichloromethane gradient afforded material which was homogeneous by TLC, but which was difficult to dry. After co-evaporating the chromatographed product several times with chloroform and vacuum-drying, 536.5 mg of alkynylamino nucleoside 22 was obtained as a white foam. This material was homogeneous by TLC and was pure by NMR except for a small amount (39 mole%; corrected yield 66%) of chloroform.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05242796uspto-grants-1993_09