12-Trifluoroacetamido-1-dodecyne → 5-(12-Trifluoroacetamido1-dodecynyl)-2',3'-dideoxyuridine

HRID 1886513Notes

Reaction equation

HRID 1886513 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[CH:17])=[O:4].I[C@@:21]1([N:30]2[CH:37]=[CH:36][C:34](=[O:35])[NH:33][C:31]2=[O:32])[O:29][C@H:26]([CH2:27][OH:28])[C@@H:24](O)[C@H:22]1O>>[F:1][C:2]([F:18])([F:19])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:36]1[C:34](=[O:35])[NH:33][C:31](=[O:32])[N:30]([CH:37]=1)[C@@H:21]1[O:29][C@H:26]([CH2:27][OH:28])[CH2:24][CH2:22]1)=[O:4]

Participants

3

Reactant 2

HCID 1987634012-Trifluoroacetamido-1-dodecyneHCID 66601875Iodouridine

Product 1

HCID 147685455-(12-Trifluoroacetamido1-dodecynyl)-2',3'-dideoxyuridine

Procedure

Protected alkynylamine 63 was coupled for 24 h to 5-iodo-2',3'-dideoxyuridine (47, 676.2 mg, 2.00 mmol, prepared as described in Example 2A) following the general procedure described in Example 1C. Chromatography on silica gel (100 g) eluting with a 0-5% methanol in dichloromethane gradient afforded a dark red foam. The red impurity was removed by chromatography on a reverse phase column (100 g, octadecylsilane on 40 micrometer silica gel, Baker) with 40% water in methanol. The appropriate fractions were combined, concentrated, and co-evaporated twice with absolute ethanol to afford 731 mg of alkynylamino nucleoside 60 as a clear oil. This material was homogeneous by TLC and NMR except for the presence of residual ethanol (25 mole %, corrected yield 73%).

Workup

  1. washChromatography on silica gel (100 g) eluting with a 0-5% methanol in dichloromethane gradient
  2. customafforded a dark red foam
  3. customThe red impurity was removed by chromatography on a reverse phase column (100 g, octadecylsilane on 40 micrometer silica gel, Baker) with 40% water in methanol
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-deb1f0e5caaa4ad69c344a4a5e18940b
Source dataset
uspto-grants-1992_09
Patent number
US05151507

Reaction notes

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