Water → HCID 19956163, compound

HRID 1779434Notes

Reaction equation

S(Cl)(Cl)=O.[OH:5][C:6]([CH3:12])([CH2:10][CH3:11])[C:7](O)=[O:8].[NH2:13][C:14]1[S:15][C:16]([C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])=[N:17][N:18]=1.O>CN(C)C(=O)C>[C:21]1([C:19]([C:16]2[S:15][C:14]([NH:13][C:7](=[O:8])[C:6]([OH:5])([CH3:12])[CH2:10][CH3:11])=[N:18][N:17]=2)=[O:20])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Thionyl chloride (60 μl, 0.82 mmol) is added to 2-hydroxy-methylbutyric acid (96.0 mg, 0.813 mmol) in 5.0 ml of N,N-dimethylacetamide at -20°/-15° C. and the mixture is stirred at -15°/-10° C. for one hour. After adding 2-amino-5-(phenylcarbonyl)-1,3,4-thiadiazole (102.3 mg, 0.499 mmol) and equilibrating the reaction mixture to room temperature, it is stirred overnight. The reaction mixture is poured into 100 ml of water and subjected to extraction with 3×25 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and filtered and the solvent is distilled off. The oil which remains is purified by flash chromatography (eluent: 33% v/v ethyl acetate in petroleum ether (40/60)).

Workup

customto room temperature
stirringit is stirred overnight
extractionsubjected to extraction with 3×25 ml of ethyl acetate
dry with materialThe combined organic phases are dried over magnesium sulfate
filtrationfiltered
distillationthe solvent is distilled off
customThe oil which remains is purified by flash chromatography (eluent: 33% v/v ethyl acetate in petroleum ether (40/60))

Sources & evidence

ORD record: ord-d0fccd40d0e3444ba2f2243de2b138cd
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05627198

Reaction notes

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