Tributyltin azide → 3-Tetrazolyl-2-(1,1-dimethylethoxy)methanamidopropionic acid

HRID 2396445노트

반응식

HRID 2396445 반응식
[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]1

참가 물질

4

반응물 2

HCID 4984872Tributyltin azideHCID 145856242-{[(Tert-butoxy)carbonyl]amino}-3-cyanopropanoic acid

생성물 1

HCID 1784533493-Tetrazolyl-2-(1,1-dimethylethoxy)methanamidopropionic acid수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

17.5 g (82 mmol, 1 equiv.) of the compound of Example 39 (3-cyano-2-(1,1-dimethylethoxy)methanamide-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 volatile removed in vacuo on the rotary evaporator. The residue was dissolved in 300 mL of 0.5M 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, 2 H); 1.40 p.p.m. (s, 9H). This material is suitable for use in solid-phase peptide synthesis.

후처리

  1. temperatureto reflux
  2. temperatureThe reaction mixture was cooled
  3. customthe volatile removed in vacuo on the rotary evaporator
  4. dissolutionThe residue was dissolved in 300 mL of 0.5M NaOH
  5. washthis aqueous solution was washed with ethyl acetate (4×100 mL)
  6. washthe resin washed with four column volumes of 1:1 methanol
  7. customThe volatiles were removed in vacuo on the rotary evaporator

출처 및 근거

ORD 기록
ord-f49ccbb84116459f82c8aa747167e887
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05492895

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