Hydrochloric Acid → 4-[({[4-(Aminocarbonyl)-3-(4-nitrophenyl)isothiazol-5-yl]amino}carbonyl)amino]butanoic acid

HRID 871011Notes

Reaction equation

HRID 871011 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([C:15]([NH2:17])=[O:16])=[C:13]([NH:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:26])=[O:20])[S:12][N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[OH-:28].[Na+]>>[NH2:17][C:15]([C:14]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:11][S:12][C:13]=1[NH:18][C:19]([NH:21][CH2:25][CH2:24][CH2:23][C:22]([OH:28])=[O:26])=[O:20])=[O:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 716216273-(4-Nitro-phenyl)-5-[(2-oxo-pyrrolidine-1-carbonyl)-amino]-isothiazole-4-carboxylic acid amide

Product 1

HCID 716216314-[({[4-(Aminocarbonyl)-3-(4-nitrophenyl)isothiazol-5-yl]amino}carbonyl)amino]butanoic acid

Procedure

3-(4-Nitro-phenyl)-5-[(2-oxo-pyrrolidine-1-carbonyl)-amino]-isothiazole-4-carboxylic acid amide (12.5 g) added to 1 N sodium hydroxide (250 mL) at ambient temperature. The resulting mixture was stirred at ambient temperature for overnight (reaction mixture clear solution). Reaction mixture acidified with 2 N HCl. The solid which formed was collected by filtration and washed with water then dried in vacuo to give the title compound as off white solid (11.5 g, 88%).

Workup

  1. custom(reaction mixture clear solution)
  2. customReaction mixture
  3. customThe solid which formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customthen dried in vacuo

Sources & evidence

ORD record
ord-4cb8f22c222d4e7da498de3c520caf06
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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