Methanol → 5-(5-Trifluoroacetamido-1-pentynyl)2',3'dideoxyuridine

HRID 1886511Notes

Reaction equation

HRID 1886511 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C:9]#[CH:10])=[O:4].I[C@@:14]1([N:23]2[CH:30]=[CH:29][C:27](=[O:28])[NH:26][C:24]2=[O:25])[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17](O)[C@H:15]1O.CO>ClCCl>[F:1][C:2]([F:11])([F:12])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C:9]#[C:10][C:29]1[C:27](=[O:28])[NH:26][C:24](=[O:25])[N:23]([CH:30]=1)[C@@H:14]1[O:22][C@H:19]([CH2:20][OH:21])[CH2:17][CH2:15]1)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 15817624HCID 15817624, compoundHCID 66601875Iodouridine

Product 1

HCID 147685435-(5-Trifluoroacetamido-1-pentynyl)2',3'dideoxyuridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Trifluroacetamido-1-pentyne (59) was coupled for 4 h to 5-iodo-2',3'-dideoxyuridine (47, prepared as described in Example 2A) according to the general procedure described in Example 1C. Chromatography on silica gel (100 g) with a 0-5% methanol in dichloromethane gradient afforded 647.7 mg of alkynylamino nucleoside 58 as a light tan foam. This material was homogeneous by TLC and NMR except for the presence of about 16 mole % of dimethylformamide. Correcting for the presence of dimethylformamide, the yield of desired product was 80%.

Sources & evidence

ORD record
ord-f17bfd84248b42cb88f318f3d3fce0e1
Source dataset
uspto-grants-1992_09
Patent number
US05151507

Reaction notes

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