Tributyltin azide → HCID 178500079, compound

HRID 1419453Notes

Reaction equation

HRID 1419453 reaction equation
[C:1]([CH2:3][CH:4]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:5]([O:7][CH3:8])=[O:6])#[N:2].C([Sn]([N:33]=[N+:34]=[N-:35])(CCCC)CCCC)CCC>C1COCC1>[NH:33]1[C:1]([CH2:3][CH:4]([NH:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C:5]([O:7][CH3:8])=[O:6])=[N:2][N:35]=[N:34]1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 85288668HCID 85288668, compound

Product 1

HCID 178500079HCID 178500079, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 g (9.54 mmol, 1 equiv.) of the compound of Example 51 (3-cyano-2-benzyloxymethanamidopropionic acid, methyl ester) was dissolved in 10 mL of dry THF and 3.0 g (9.54 mmol, 1 equiv.) of tri-n-butyltin azide was added. The reaction was refluxed for 72 hours followed by concentration in vacuo. 50 mL of 1M NaOH was added and the aqueous solution was extracted with ethyl acetate (3×50 mL). The aqueous solution was acidified to pH=1 with 4M HCl and extracted with ethyl acetate (4×60 mL). After drying over sodium sulfate, the organics were decanted and concentrated an vacuo to yield 2.5 g of the title compound. 1H-NMR (CDCl3): 7.3 p.p.m (m, 5H); 6.1 p.p.m. (m, 1H); 5.1 p.p.m. (s, 2H); 4.8 p.p.m. (m, 1H); 3.8 p.p.m. (s, 3H); 3.5 p.p.m. (m, 2H).

Workup

  1. temperatureThe reaction was refluxed for 72 hours
  2. concentrationfollowed by concentration in vacuo
  3. addition50 mL of 1M NaOH was added
  4. extractionthe aqueous solution was extracted with ethyl acetate (3×50 mL)
  5. extractionextracted with ethyl acetate (4×60 mL)
  6. dry with materialAfter drying over sodium sulfate
  7. customthe organics were decanted
  8. concentrationconcentrated an vacuo

Sources & evidence

ORD record
ord-6324782443d14665a4296f3f5919a2b2
Source dataset
uspto-grants-1999_03
Patent number
US05886146

Reaction notes

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