Methanol → 5-TFA-ap-ddU

HRID 743958Notes

Reaction equation

HRID 743958 reaction equation
I[C@@:2]1([N:11]2[CH:18]=[CH:17][C:15](=[O:16])[NH:14][C:12]2=[O:13])[O:10][C@H:7]([CH2:8][OH:9])[C@@H:5](O)[C@H:3]1O.[CH2:19]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[C:20]#[CH:21].CO>ClCCl>[F:25][C:24]([F:27])([F:26])[C:23]([NH:22][CH2:19][C:20]#[C:21][C:17]1[C:15](=[O:16])[NH:14][C:12](=[O:13])[N:11]([CH:18]=1)[C@@H:2]1[O:10][C@H:7]([CH2:8][OH:9])[CH2:5][CH2:3]1)=[O:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 110948052,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamideHCID 66601875Iodouridine

Product 1

HCID 147685415-TFA-ap-ddU

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customto dry
  2. customvacuum-drying

Sources & evidence

ORD record
ord-83af95cd70364671a75ba48b6139e921
Source dataset
uspto-grants-1996_09
Patent number
US05558991

Reaction notes

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