Azido(trimethyl)stannane → HCID 178451571, compound

HRID 1902169Notes

Reaction equation

HRID 1902169 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]#[N:23])=[CH:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].C[Sn]([N:28]=[N+:29]=[N-:30])(C)C>C1(C)C=CC=CC=1>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[NH:30][N:29]=[N:28][N:23]=3)=[CH:14]2)[CH2:12][CH2:13]1)=[O:7])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 70344591HCID 70344591, compound

Product 1

HCID 178451571HCID 178451571, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the title compound from Step A (298 mg, 0.96 mmol) in toluene was added trimethylstannyl azide (787 mg, 3.84 mmol). The mixture was refluxed for 18 hours and then cooled and 1N HCL was added. The aqueous layer was extracted with ethyl acetate (3×1 vol) and the organic layer was washed with water, brine, dried over magnesium sulfate and concentrated. Purification by MPLC (LH20 column methanol) provided the title compound (214 mg, 0.60 mmol).

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperaturecooled
  3. addition1N HCL was added
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×1 vol)
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customPurification by MPLC (LH20 column methanol)

Sources & evidence

ORD record
ord-4318ba68ae6349459c5814b72426c8c7
Source dataset
uspto-grants-1996_11
Patent number
US05578593

Reaction notes

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