Dimethylformamide → HCID 86586412, compound

HRID 1266577Notes

Reaction equation

[CH3:1][CH:2]([CH3:22])[C@@H:3]([NH:7][S:8]([C:11]1[CH:21]=[CH:20][C:14]2[N:15]=[C:16]([S:18][CH3:19])[S:17][C:13]=2[CH:12]=1)(=[O:10])=[O:9])[C:4](O)=[O:5].C(Cl)(=O)C([Cl:26])=O.CN(C=O)C>ClCCl>[CH3:1][CH:2]([CH3:22])[C@@H:3]([NH:7][S:8]([C:11]1[CH:21]=[CH:20][C:14]2[N:15]=[C:16]([S:18][CH3:19])[S:17][C:13]=2[CH:12]=1)(=[O:10])=[O:9])[C:4]([Cl:26])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

(2R)-3-methyl-2-[(2-methylthiobenzthiazol-6-sulfonyl)amino]butanoic acid (54 mg, 0.15 mmol) prepared in Example 14 was dissolved in dichloromethane (2 mL) and cooled down to 0° C., and added oxalylchloride (0.04 mL, 3 equi.) and DMF of catalytic amount. The reaction solution was subjected at room temperature for 3 hours. Then, the reaction solution was distilled and dried under reduced pressure to remove the solvent. And then, (2R)-3-methyl-2-[(2-methylthiobenzthiazol-6-sulfonyl) amino]butanoic chloride thus obtained was dissolved in THF (1 mL). Hydroxylamine hydrochloride (0.11 g, 10 equi.) and NaHCO3 (0.15 g, 12 equi.) were dissolved in THF/H2O (1 mL/1 ml) and cooled down to 0° C. The above acid chloride THF solution was slowly added to hydroxylamine solution while maintaining the temperature of 0° C. The solvent was removed from the reaction solution after 1 hour. Then, the product was extracted with ethylacetate (5 mL) and washed with H2O and 0.1N HCl, dried over MgSO4, distilled under reduced pressure and dried under vacuum, to prepare the titled compound, (2R)-N-hydroxy-3-methyl-2-[(2-methylthiobenzthiazol-6-sulfonyl)amino]butyric amide(50 mg, 90%).

Workup

distillationThen, the reaction solution was distilled
customdried under reduced pressure
customto remove the solvent

Sources & evidence

ORD record: ord-f257690806b2449895fb388c3b799d37
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548667B2

Reaction notes

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