Dimethylformamide → HCID 86586418, compound

HRID 1266585Notes

Reaction equation

[CH2:1]([S:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([S:16]([NH:19][C@H:20]([CH3:24])[C:21](O)=[O:22])(=[O:18])=[O:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(Cl)(=O)C([Cl:28])=O.CN(C=O)C>ClCCl>[CH2:1]([S:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([S:16]([NH:19][C@H:20]([CH3:24])[C:21]([Cl:28])=[O:22])(=[O:18])=[O:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

(2R)-2-[(2-n-pentylthiobenzthiazol-6-sulfonyl) amino]propionic acid (190 mg, 0.49 mmol) prepared in Example 29 was dissolved in dichloromethane (2 mL) and cooled down to 0° C. Oxalylchloride (0.17 mL, 4 equi.) and DMF of catalytic amount were added and the reaction solution was refluxed for 3 hours at RT. Then, the solution was distilled under reduced pressure to remove the solvent and dried under reduced pressure to give (2R)-2-[(2-n-pentylthiobenzthiazol-6-sulfonyl)amino]propionic chloride. And then, the compound was dissolved in THF (2 mL) to obtain acid chloride THF solution. Hydroxyamine hydrochloride salt (0.34 g, 10 equi.) and NaHCO3 (0.49 g, 12 equi.) was dissolved in THF/H2O (1 mL/1 mL) and cooled down to 0° C. Acid chloride THF solution was slowly added to hydroxyamine solution at 0° C., and the solvent was removed after 1 hour. Then, the product was extracted with ethylacetate (5 mL), washed with H2O and 0.1N HCl, dried over MgSO4, distilled and vacuum-dried to prepare the titled compound, (2R)-N-hydroxy-2-[(2-n-pentylthiobenzthiazol-6-sulfonyl)amino] propion amide (190 mg, 97%).

Workup

temperaturethe reaction solution was refluxed for 3 hours at RT
distillationThen, the solution was distilled under reduced pressure
customto remove the solvent
customdried under reduced pressure

Sources & evidence

ORD record: ord-4db3a108496b437490a78b16e7df7f73
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548667B2

Reaction notes

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