Diethyl Ether → HCID 68697763, compound

HRID 2244364Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:9](=[S:14])[NH:10][CH:11]1[CH2:13][CH2:12]1)=[C:6]([NH2:8])[CH3:7])[CH3:2].BrBr.C(OCC)C.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:5]1[C:6]([CH3:7])=[N:8][S:14][C:9]=1[NH:10][CH:11]1[CH2:13][CH2:12]1)=[O:15])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a vigorously stirred solution of 1 g of 3-amino-2-cyclopropylthiocarbamoyl-but-2-enoic acid ethyl ester (4.4 mmol) in chloroform (16 ml) was added dropwise a solution of 1.4 g of bromine in chloroform (8 ml) at 0° C. After completion of the addition the reaction mixture was stirred at 0° C. for additional 5 min. Then diethyl ether and sat. NaHCO3-solution were added and the mixture was extracted with diethyl ether. The combined extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography (100% DCM) to give 5-cyclopropylamino-3-methyl-isothiazole-4-carboxylic acid ethyl ester (410 mg, 40%) as a brown liquid. 1HNMR (CDCl3, 300 MHz): δ 0.73 (m, 2H), 0.81 (m, 2H), 1.36 (t, J=7.2 Hz, 3H), 2.50 (s, 3H), 2.63 (m, 1H), 4.29 (q, J=7.2 Hz, 2H), 7.80 (br s, 1H).

Workup

additionAfter completion of the addition the reaction mixture
extractionthe mixture was extracted with diethyl ether
washThe combined extracts were washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto give a residue which
customwas purified by flash column chromatography (100% DCM)

Sources & evidence

ORD record: ord-d1673a99db0a4cd58dd036d088b003a2
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678818B2

Reaction notes

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