Acetic Acid → HCID 23295956, compound

HRID 361515Notes

Reaction equation

HRID 361515 reaction equation
[OH:1][CH:2]([CH2:19]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH:14]=[CH:13][N:12]([CH3:17])[C:11]1=[O:18].[BrH:21].[C:22]([OH:25])(=O)[CH3:23].C(=O)(O)[O-].[Na+]>ClCCl.O>[C:22]([O:1][CH:2]([CH2:19][Br:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH:14]=[CH:13][N:12]([CH3:17])[C:11]1=[O:18])(=[O:25])[CH3:23]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 23287933HCID 23287933, compound

Product 1

HCID 23295956HCID 23295956, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(8,9-dihydroxynonyl)-1-methyluracil (2.15 g, 7.6 mmol) and a 30% solution of hydrogen bromide in acetic acid (4.5 mL, 23 mmol) were stirred for 6 hours. The reaction mixture was added slowly to a mixture of sodium bicarbonate (8.4 g, 0.1 mol), water (30 mL), and dichloromethane (30 mL). The layers were separated, and the aqueous layer extracted with dichloromethane (3×40 mL). The combined organic layers were washed with aqueous saturated salt solution (20 mL) and dried over sodium sulfate. The solvent was removed under vacuum to yield 2.89 g (97% yield) 3-(8-acetoxy-9-bromononyl)-1-methyluracil (inventive compound no. 1801) as a thick, slightly orange oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with dichloromethane (3×40 mL)
  3. washThe combined organic layers were washed with aqueous saturated salt solution (20 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-5278eb998bee431cb79a4ff0c12f4602
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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