Ethylthiol trifluoroacetate → 2'-TFA-NH-dU

HRID 618964Notes

Reaction equation

HRID 618964 reaction equation
[NH2:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[O:12].[F:18][C:19]([F:26])([F:25])[C:20](SCC)=[O:21]>CO>[F:18][C:19]([F:26])([F:25])[C:20]([NH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[O:12])=[O:21]

Participants

4

Reactant 2

HCID 67844Ethylthiol trifluoroacetateHCID 64824792'-Amino-2'-deoxyuridine

Product 1

HCID 149901442'-TFA-NH-dUYield 82.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2'-amino,2'-deoxyuridine (2.0 g, 8.22 mmoles) in methanol (150 ml) was added S-ethyl trifluorothioacetate (1.6 ml, 12.48 mmoles, 1.5 eq.). This mixture was stirred at room temperature overnight. Nitrogen was bubbled through the reaction mixture for 2 h to remove volatile thio-byproducts. The mixture was evaporated to dryness and the solid was recrystallized from methanol/chloroform to yield 2.3 g (82%) of 2'-trifluoroacetylamino,2'-deoxyuridine. The analytical data agreed with the literature (Imazawa and Eckstein (1979) supra).

Workup

  1. customNitrogen was bubbled through the reaction mixture for 2 h
  2. customto remove volatile thio-byproducts
  3. customThe mixture was evaporated to dryness
  4. customthe solid was recrystallized from methanol/chloroform

Sources & evidence

ORD record
ord-db3d002fe52248e1abf38595c0e24f37
Source dataset
uspto-grants-1999_09
Patent number
US05958691

Reaction notes

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