2-Bromophenylacetyl chloride → 4-N-benzoyl-5'-[2-(2-bromophenyl)acetamido]-2',5'-dideoxy-5-ethylcytidine

HRID 232355Notes

Reaction equation

HRID 232355 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](Cl)=[O:10].[NH2:12][CH2:13][C@H:14]1[O:18][C@@H:17]([N:19]2[CH:34]=[C:33]([CH2:35][CH3:36])[C:23]([NH:24][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][C:20]2=[O:21])[CH2:16][C@@H:15]1[OH:37]>C(OCC)C.[OH-].[Na+]>[C:25]([NH:24][C:23]1[C:33]([CH2:35][CH3:36])=[CH:34][N:19]([C@@H:17]2[O:18][C@H:14]([CH2:13][NH:12][C:9](=[O:10])[CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Br:1])[C@@H:15]([OH:37])[CH2:16]2)[C:20](=[O:21])[N:22]=1)(=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 41383862-Bromophenylacetyl chlorideHCID 186334605'-amino-4-N-benzoyl-2',5'-dideoxy-5-ethylcytidine

Product 1

HCID 186334534-N-benzoyl-5'-[2-(2-bromophenyl)acetamido]-2',5'-dideoxy-5-ethylcytidineYield 20%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 210 mg of (2-bromophenyl)acetyl chloride in 3 ml of diethyl ether was added to a solution of 324 mg of 5'-amino-4-N-benzoyl-2',5'-dideoxy-5-ethylcytidine in 4.9 ml of 0.18M sodium hydroxide solution and the mixture was shaken vigorously for 10 minutes. The solid was collected by filtration, washed with 2 ml of water and 1 ml of diethyl ether and recrystallized from 15 ml of ethanol to give 100 mg of 4-N-benzoyl-5'-[2-(2-bromophenyl)acetamido]-2',5'-dideoxy-5-ethylcytidine in the form of a white solid which was processed further without purification.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with 2 ml of water and 1 ml of diethyl ether
  3. customrecrystallized from 15 ml of ethanol

Sources & evidence

ORD record
ord-49277f14e1584027b30aea3c3f3b525d
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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