p-Toluenesulfonyl azide → HCID 86755102, compound

HRID 376594Notes

Reaction equation

HRID 376594 reaction equation
[O:1]=[C:2]([CH2:16][CH2:17][CH:18]1[NH:21][C:20](=[O:22])[CH:19]1[NH:23][C:24](=[O:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:5].O=C(CCC1NC(=O)C1NC(=O)COC1C=CC=CC=1)CC(OCC1C=CC([N+]([O-])=O)=CC=1)=O.C1(C)C=CC(S([N:76]=[N+:77]=[N-])(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C>C(#N)C>[N+:76](=[C:3]([C:2](=[O:1])[CH2:16][CH2:17][CH:18]1[NH:21][C:20](=[O:22])[CH:19]1[NH:23][C:24](=[O:32])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:5])=[N-:77]

Participants

6

Reactant 4

HCID 13661p-Toluenesulfonyl azideHCID 81531DiisopropylethylamineHCID 14380014HCID 14380014, compoundHCID 19700557HCID 19700557, compound

Product 1

HCID 86755102HCID 86755102, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-methoxybenzyl 3-oxo-5-[(3SR,4RS)-3-phenylacetamidoazetidin-2-on-4-yl]pentanoate (1.38g, 3.15mmol) [prepared by the method described for 4-nitrobenzyl 3-oxo-5-[(3SR,4RS)-3-phenoxyacetamidoazetidin-2-on-4-yl]pentanoate, C. Bodurow and M. A. Carr, Tetrahedron Lett., 1989, 30, 4801] in acetonitrile (60ml) was treated with 4-toluenesulphonyl azide (870mg, 4.42mmol) and N,N-diisopropylethylamine (822μl, 4.73mmol) at 0° C. After 10 min., the ice-bath was removed and stirring was continued at room temperature for 2h. The reaction mixture was diluted with ethyl acetate and washed with brine. After drying over MgSO4, the solvent was evaporated in vacuo and the residue purified by chromatography on silica gel eluting with ethyl acetate to yield the title compound (1.27g, 87%); vmax (KBr) 2134, 1775, 1717, 1654, 1513 and 1304cm-1 ; δH (CDCl3, 250MHz) 1.59-1.70 (2H,m), 2.68-2.95 (2H,m), 3.55 and 3.65 (2H, ABq, J 15.6Hz), 3.78 (1H,m), 3.82 (3H,s), 5.19 (2H,s), 5.25 (1H, ddd, J 8.1, 4.9, 1.0Hz), 6.25 (1H, br s, exch.), 6.49 (1H, br d, J 8.1Hz, exch.), 6.90 (2H,d, J 8.7Hz) and 7.23-7.70 (7H,m). [Mass spectrum : +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (487)].

Workup

  1. customthe ice-bath was removed
  2. waitwas continued at room temperature for 2h
  3. additionThe reaction mixture was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialAfter drying over MgSO4
  6. customthe solvent was evaporated in vacuo
  7. customthe residue purified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-02be39174956433ca24f1c5e3c3d563b
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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