Azido(trimethyl)stannane → HCID 178438841, compound

HRID 1378880Notes

Reaction equation

HRID 1378880 reaction equation
[K].[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15](=[O:38])[CH:16]([C:29]2[CH:34]=[CH:33][C:32]3[O:35][CH2:36][O:37][C:31]=3[CH:30]=2)[O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=2[CH2:26][CH2:27][CH3:28])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C[Sn]([N:43]=[N+:44]=[N-:45])(C)C>C1(C)C=CC=CC=1>[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15](=[O:38])[CH:16]([C:29]2[CH:34]=[CH:33][C:32]3[O:35][CH2:36][O:37][C:31]=3[CH:30]=2)[O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[NH:45][N:44]=[N:43][N:25]=3)=[CH:20][C:19]=2[CH2:26][CH2:27][CH3:28])(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 131719618HCID 131719618, compound

Product 1

HCID 178438841HCID 178438841, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 600 mg (1.15 mmol) of the product of Example 151, Step F and 284 mg (1.38 mmol) of trimethyltin azide in 2 mL of toluene was heated with an oil bath at reflux overnight. The reaction was evaporated in vacuo, purified by silica gel flash chromatography eluting with methylene chloride/methanol/acetic acid 100:3:1, and the purified fractions concentrated in vacuo to afford 244 mg (38%) of the title compound as an amorphous solid.

Workup

  1. temperatureat reflux overnight
  2. customThe reaction was evaporated in vacuo
  3. custompurified by silica gel flash chromatography
  4. washeluting with methylene chloride/methanol/acetic acid 100:3:1
  5. concentrationthe purified fractions concentrated in vacuo

Sources & evidence

ORD record
ord-e59126ebc6774318aa8758a5e48a3ab4
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Reaction notes

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