5'-Amino-5'-deoxythymidine → HCID 54041648, compound

HRID 232343Notes

Reaction equation

HRID 232343 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][CH2:12][C@H:13]1[O:17][C@@H:16]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:15][C@@H:14]1[OH:27]>C(OCC)C.[OH-].[Na+]>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][CH2:12][C@H:13]2[O:17][C@@H:16]([N:18]3[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]3=[O:20])[CH2:15][C@@H:14]2[OH:27])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 653115'-Amino-5'-deoxythymidineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 54041648HCID 54041648, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 219 mg of 4-bromobenzoyl chloride in 5 ml of diethyl ether was added to a solution of 241 mg of 5'-amino-5'-deoxythymidine in 4 ml of 0.25M sodium hydroxide solution and the mixture was shaken vigorously for 10 minutes. The mixture was filtered and the solid was washed with 10 ml of water and 4 ml of diethyl ether, and recrystallized from ethanol to give 195 mg of 5'-(4-bromobenzamido)-5'-deoxythymidine of melting point 250.5°-252° C.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with 10 ml of water and 4 ml of diethyl ether
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-04e2a1b1f1cc43a2a7ea0f2341c97d49
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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