Dimethylformamide → HCID 86586412, compound

HRID 1266586Notes

Reaction equation

HRID 1266586 reaction equation
[CH2:1]([S:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([S:16]([N:19]([CH2:25][C:26]3[CH:31]=CC=C[CH:27]=3)[C@H](C)C(O)=O)(=[O:18])=[O:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)CCCC.C(Cl)(=O)[C:33]([Cl:35])=[O:34].CN(C=O)C>ClCCl>[CH3:31][CH:26]([CH3:27])[C@@H:25]([NH:19][S:16]([C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([S:6][CH3:1])[S:8][C:9]=2[CH:15]=1)(=[O:17])=[O:18])[C:33]([Cl:35])=[O:34]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10140557HCID 10140557, compound

Product 1

HCID 86586412HCID 86586412, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2R)-2-[(2-n-pentylthiobenzthiazol-6-sulfonyl) benzylamino]propionic acid (157 mg, 0.328 mmol) prepared in Example 33 was dissolved in dichloromethane (2 mL) and cooled down to 0° C. Oxalylchloride (0.114 mL, 10 equi.) and DMF of catalytic amount were added and the reaction solution was refluxed for 3 hours at RT. After reaction, the solution was distilled under reduced pressure to remove the solvent and dried under reduced pressure to give (2R)-3-methyl-2-[(2-methylthiobenzthiazol-6-sulfonyl)amino]butanoic chloride. The compound was then dissolved in THF (1 mL) to obtain acid chloride THF solution. Hydroxyamine hydrochloride salt (0.23 g, 10 equi.) and NaHCO3 (0.33 g, 12 equi.) were dissolved in THF/H2O (3 mL/3 mL) and cooled down to 0° C. to give a hydroxyamine solution. The above acid chloride THF solution was slowly added to the hydroxyamine solution at 0° C. After 1 hour, the solvent was removed from the reaction solution. Then, the product was extracted with ethylacetate 10 mL), washed with H2O and 0.1N HCl, dried over MgSO4, distilled under reduced pressure and vacuum-dried to prepare the titled compound, (2R)-N-hydroxy-2-[(2-n-pentylthiobenzthiazol-6-sulfonyl)benzylamino]propionamide (163 mg, 100%).

Workup

  1. temperaturethe reaction solution was refluxed for 3 hours at RT
  2. customAfter reaction
  3. distillationthe solution was distilled under reduced pressure
  4. customto remove the solvent
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c95797145c7646e3bdd230a51e5c1fb7
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

Loading…