Ammonium formate → 5-[3-(2-Trifluoroacetamidoethoxy)propyl]2'-deoxyuridine

HRID 1416388Notes

Reaction equation

HRID 1416388 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]([NH:5][CH2:6][CH2:7][O:8][CH2:9][C:10]#[C:11][C:12]1[C:13](=[O:27])[NH:14][C:15](=[O:26])[N:16]([CH:25]=1)[C@@H:17]1[O:24][C@H:21]([CH2:22][OH:23])[C@@H:19]([OH:20])[CH2:18]1)=[O:4].C([O-])=O.[NH4+]>CO.[Pd]>[F:28][C:2]([F:1])([F:29])[C:3]([NH:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[C:13](=[O:27])[NH:14][C:15](=[O:26])[N:16]([CH:25]=1)[C@@H:17]1[O:24][C@H:21]([CH2:22][OH:23])[C@@H:19]([OH:20])[CH2:18]1)=[O:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 213095685-[3-(2-Trifluoroacetamidoethoxy)propynyl]-2'-deoxyuridine

Product 1

HCID 544222105-[3-(2-Trifluoroacetamidoethoxy)propyl]2'-deoxyuridineYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-[3-(2-trifluoroacetamidoethoxy)propynyl]-2'-deoxyuridine (3.4 g, 8.1 mmol) in methanol (20 ml) is stirred with ammonium formate (prepared by addition of 3 ml, 79 mmol of cold 98% formic acid into 2 ml, 50 mmol of dry ice frozen 25% ammonia) and 0.2 g of 10% Pd/C for 7 hours at room temperature under hydrogen atmosphere. The catalyst is removed by filtration, the filtrate evaporated and product is purified on LiChroprep RP-18 column by the above procedure. Fractions containing the desired product are combined and evaporated to dryness in vacuo and the resultant solid is triturated with dry ether to give 3.0 g (87% product, m.p. 107-110°; max in nm, in 0.1M triethylamine-acetate (pH 7.5), 220, 268. Analysis calculated for C16H22F3N3O7 : C, 45.18; H, 5.21; N, 9.88; F, 13.40. Found C, 45.16; H, 5.16; N, 9.68; F, 13.13.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate evaporated
  3. customproduct is purified on LiChroprep RP-18 column by the above procedure
  4. additionFractions containing the desired product
  5. customevaporated to dryness in vacuo
  6. customthe resultant solid is triturated with dry ether

Sources & evidence

ORD record
ord-336d066d64ad4ab29d6f9a9e34e87817
Source dataset
uspto-grants-1999_06
Patent number
US05912340

Reaction notes

Loading…