Sodium Hydroxide → 5-Bromo-5'-[2-(2-bromophenyl)acetamido]-2',5'-dideoxycytidine

HRID 232346Notes

Reaction equation

HRID 232346 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([Br:18])[C:14]([NH2:15])=[N:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[OH:19].[Br:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28](Cl)=[O:29]>O.ClCCl>[Br:18][C:16]1[C:14]([NH2:15])=[N:13][C:11](=[O:12])[N:10]([CH:17]=1)[C@@H:8]1[O:9][C@H:5]([CH2:4][NH:3][C:28](=[O:29])[CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[Br:20])[C@@H:6]([OH:19])[CH2:7]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 41383862-Bromophenylacetyl chlorideHCID 539167865'-Amino-5-bromo-2',5'-dideoxycytidine

Product 1

HCID 540625325-Bromo-5'-[2-(2-bromophenyl)acetamido]-2',5'-dideoxycytidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.84 ml of a 1M sodium hydroxide solution was added to a solution of 256 mg of 5'-amino-5-bromo-2',5'-dideoxycytidine in 3.3 ml of water. A solution of (2-bromophenyl)acetyl chloride (prepared from 185 mg of the acid) in 5 ml of dichloromethane was added, the mixture was shaken vigorously for 10 minutes and then filtered. The solid was recrystallized from 30 ml of ethanol to give 44 mg of 5-bromo-5'-[2-(2-bromophenyl)acetamido]-2',5'-dideoxycytidine in the form of a white solid of melting point 164°-167° C.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. customThe solid was recrystallized from 30 ml of ethanol

Sources & evidence

ORD record
ord-62c371d9aa714acd8cb584db57fd2ba0
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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