Sodium Iodide → HCID 69494573, compound

HRID 916724Notes

Reaction equation

HRID 916724 reaction equation
[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]2[C@:8]([C:18]([F:21])([F:20])[F:19])([C:13]#[C:14][CH:15]3[CH2:17][CH2:16]3)[O:9][C:10]([NH:12][C:3]=2[CH:2]=1)=[O:11].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[C:30]([O:34][C:35](=[O:40])[CH2:36][CH2:37][CH2:38]Br)([CH3:33])([CH3:32])[CH3:31]>C1OCCOCCOCCOCCOCCOC1.CN(C=O)C>[C:30]([O:34][C:35](=[O:40])[CH2:36][CH2:37][CH2:38][N:12]1[C:3]2[CH:2]=[CH:1][C:6]([Cl:7])=[CH:5][C:4]=2[C:8]([C:13]#[C:14][CH:15]2[CH2:16][CH2:17]2)([C:18]([F:20])([F:21])[F:19])[O:9][C:10]1=[O:11])([CH3:33])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 64139EfavirenzHCID 2757253tert-Butyl 4-bromobutanoate

Product 1

HCID 69494573HCID 69494573, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To 250 mg (0.79 mmol) of efavirenz 1 was added 10 mL of anhydrous DMF, 600 mg (4.34 mmol) of potassium carbonate, 120 mg (0.80 mmol) of sodium iodide and 492 mg (2.2 mmol) of 4-bromo-butyric acid tert-butyl ester followed by 5 mg of 18-crown-6. The mixture was heated to 125° C. for 2 hours under argon atmosphere and concentrated under reduced pressure. To the residue 50 mL of chloroform was added, and the solid was filtered off. To the filtrate 50 mL of water was added. The organic layer was separated, washed with 50 mL of water, dried (Na2SO4), and concentrated. The residue was purified by silica gel flash column chromatography in 70% ethyl acetate in hexane to give 327 mg (0.721 mmol, 90% yield) of 2 (M+Na, 480).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue 50 mL of chloroform was added
  3. filtrationthe solid was filtered off
  4. additionTo the filtrate 50 mL of water was added
  5. customThe organic layer was separated
  6. washwashed with 50 mL of water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel flash column chromatography in 70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5157591713fa45adb5e84b453d9982ae
Source dataset
uspto-grants-2007_09
Patent number
US07271252B2

Reaction notes

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