Tributyltin azide → 3-Tetrazolyl-2-(1,1-dimethylethoxy)methanamidopropionic acid
Reaction equation
[C:1]([CH2:3][CH:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5]([OH:7])=[O:6])#[N:2].C([Sn]([N:29]=[N+:30]=[N-:31])(CCCC)CCCC)CCC>C1COCC1>[NH:29]1[C:1]([CH2:3][CH:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5]([OH:7])=[O:6])=[N:2][N:31]=[N:30]1Participants
Procedure
17.5 g (82 mmol, 1 equiv.) of the compound of Example 39 (3-cyano-2-(1,1-dimethylethoxy)methanamido-propionic acid) was dissolved in 125 mL of THF and 40.5 g (129 mmol, 1.5 equiv.) tributyltin azide was added. The reaction mixture was brought to reflux and held there for 3 days. The reaction mixture was cooled and the volatiles removed in vacuo on the rotary evaporator. The residue was dissolved in 300 mL of 0.5 M NaOH and this aqueous solution was washed with ethyl acetate (4×100 mL). The aqueous layer was passed through a 125 mL bed of Dowex 50X8-400 ion exchange resin and the resin washed with four column volumes of 1:1 methanol:water. The volatiles were removed in vacuo on the rotary evaporator to yield 17.9 g of the title compound as a white solid (85% yield). 1H-NMR (CD3OD): 4.55 p.p.m (m, 1H); 3.40 p.p.m. (m, 2H); 1.40 p.p.m. (s, 9H). This material is suitable for use in solid-phase peptide synthesis.
Workup
- temperatureto reflux
- temperatureThe reaction mixture was cooled
- customthe volatiles removed in vacuo on the rotary evaporator
- dissolutionThe residue was dissolved in 300 mL of 0.5 M NaOH
- washthis aqueous solution was washed with ethyl acetate (4×100 mL)
- washthe resin washed with four column volumes of 1:1 methanol
- customThe volatiles were removed in vacuo on the rotary evaporator
Sources & evidence
- ORD record
- ord-fc3d524ddd68406b9d3ae05af3c7a1d9
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05955576
Reaction notes
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