Water → HCID 69116751, compound

HRID 1870475Notes

Reaction equation

HRID 1870475 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][CH2:6]/[C:7](/[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[C:8](/[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[CH:19][CH:20]=1)\[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.O.[N-]=[N+]=[N-]>CN(C=O)C>[CH3:5][CH2:6]/[C:7](/[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[C:8](/[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[CH:19][CH:20]=1)\[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1.[N-:1]=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 33558AzideHCID 131721936HCID 131721936, compound

Product 1

HCID 69116751HCID 69116751, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Into a suspension of NaN3 (260 mg, 4 mmol) in 4 ml dry DMF was added 150 mg tamoxifen tosylate (TX-OTs) (0.25 mmol). The reaction mixture was stirred at 90° C. overnight. To terminate the reaction, the vxn mixture was poured into cold water and extracted with ethyl ether (3×50 ml). The organic layers were combined and washed with H2O (2×50 ml). The ether layer was then dried over magnesium sulfate and evaporated. Further purification by flash chromatography (ether/petroleum ether/triethyl amine=5/5/1) yielded pure TX-N3. Yield 50% IR: 2150 cm-1 (Azide).

Workup

  1. customTo terminate
  2. customthe reaction
  3. extractionextracted with ethyl ether (3×50 ml)
  4. washwashed with H2O (2×50 ml)
  5. dry with materialThe ether layer was then dried over magnesium sulfate
  6. customevaporated
  7. customFurther purification by flash chromatography (ether/petroleum ether/triethyl amine=5/5/1)
  8. customyielded pure TX-N3

Sources & evidence

ORD record
ord-51088db8e1804b8687206b4978cb4bf5
Source dataset
uspto-grants-2000_08
Patent number
US06096874

Reaction notes

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