Sodium borohydride → HCID 18635825, compound

HRID 1638979Notes

Reaction equation

HRID 1638979 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][C:12](=[O:22])[CH2:13][C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:21])[O:8][C@@H:7]([N:23]2[CH:30]=[C:29]([CH2:31][CH3:32])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:6]1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(COC)OC>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][CH:12]([OH:22])[CH2:13][C:14]2[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=2[Cl:20])[O:8][C@@H:7]([N:23]2[CH:30]=[C:29]([CH2:31][CH3:32])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18635810HCID 18635810, compound

Product 1

HCID 18635825HCID 18635825, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 149 mg of 3'-O-acetyl-5'-[3-(2,6-dichlorophenyl)-2-oxopropyl]-2',5'-dideoxy-5-ethyluridine and 26 mg of sodium borohydride in 7 ml of dimethoxyethane was stirred at room temperature for 2.5 hours. The solvent was removed by evaporation and the residue was taken up in 22 ml of 5% ammonium chloride solution and extracted twice with 20 ml of ethyl acetate each time. The extracts were washed with 20 ml of water, dried over anhydrous sodium sulphate and evaporated to give 3'-O-acetyl-5'-[3-(2,6-dichlorophenyl)-2(RS)-hydroxypropyl]-2',5'-dideoxy-5-ethyluridine in the form of a colourless gum. This was dissolved in 3 ml of 0.1M sodium methoxide solution and stirred at room temperature for 1 hour. The solution was then diluted with 150 ml of methanol, stirred with a cross-linked polystyrene/divinyl benzene cation exchange resin containing sulphonic acid groups (H+ form) and then filtered. The filtrate was evaporated and the residue was crystallized from ethanol to give 45 mg of 5'-[3-(2,6-dichlorophenyl)-2(RS)-hydroxypropyl]-2' ,5'-dideoxy-5-ethyluridine, mp 185°-186° C.

Workup

  1. customThe solvent was removed by evaporation
  2. extractionextracted twice with 20 ml of ethyl acetate each time
  3. washThe extracts were washed with 20 ml of water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-8fe011d6c22d4480a24caf7855c0c29d
Source dataset
uspto-grants-1989_11
Patent number
US04882316

Reaction notes

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