Diisopropyl Ether → tert-butyl 2-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-chloro-2-oxoethylidene]amino]oxy-2-methylpropanoate;hydrochloride

HRID 1031201Notes

Reaction equation

HRID 1031201 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[NH2:7][C:8]1[S:12][N:11]=[C:10](/[C:13](=[N:17]/[O:18][C:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH3:21])[CH3:20])/[C:14](O)=[O:15])[N:9]=1.C(OC(C)C)(C)C>C(Cl)Cl>[ClH:2].[NH2:7][C:8]1[S:12][N:11]=[C:10](/[C:13](=[N:17]/[O:18][C:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH3:21])[CH3:20])/[C:14]([Cl:2])=[O:15])[N:9]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 24819Phosphorus pentachlorideHCID 13577059(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-methyl-1-((2-methylpropan-2-yl)oxy)-1-oxopropan-2-yl)oxyiminoacetic acid

Product 1

HCID 87787074tert-butyl 2-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-chloro-2-oxoethylidene]amino]oxy-2-methylpropanoate;hydrochlorideYield 144%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of phosphorus pentachloride (11.11 g) in methylene chloride (167.8 ml) was added (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetic acid (16.78 g) at -20° C. The resultant mixture was stirred at -20° to -10° C. for 1.5 hours, and to the mixture was added dropwise diisopropyl ether (671.2 ml) at -20° to -10° C. The mixture was stirred under ice-cooling for 1 hour and the resultant precipitate was collected by filtration to give (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetyl chloride hydrochloride (14.8 g).

Workup

  1. temperaturecooling for 1 hour
  2. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-f0e37026e3d347ad956af3f270ee5e67
Source dataset
uspto-grants-1992_04
Patent number
US05108997

Reaction notes

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