Triethylamine → Ethyl 2-(3,3-dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylate

HRID 1394104Notes

Reaction equation

Br.[NH2:2][C:3]1[S:4][C:5]2[CH2:11][CH2:10][CH2:9][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]=2[N:7]=1.C(N(CC)CC)C.[C:24]([CH2:28][C:29](Cl)=[O:30])([CH3:27])([CH3:26])[CH3:25]>C(#N)C>[CH3:25][C:24]([CH3:27])([CH3:26])[CH2:28][C:29]([NH:2][C:3]1[S:4][C:5]2[CH2:11][CH2:10][CH2:9][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]=2[N:7]=1)=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 2-amino-4,5,6,7-tetrahydrobenzthiazole-4-carboxyate hydrobromide (0.92 g, 0.3 mol) in acetonitrile (25 mL) there was added triethylamine (Et3N, 0.41 g, 0.4 mol). Following cooling to 0° C., tert-butylacetyl chloride (0.55 g, 0.4 mol) was slowly added, and the resultant mixture was then stirred overnight at room temperature. Following removal of the solvent and purification by column chromatography, there was obtained ethyl 2-(3,3-dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylate in a yield of 185 mg (corresponding to 19% of theory).

Workup

customremoval of the solvent and purification by column chromatography

Sources & evidence

ORD record: ord-318e770d7ce649978a8738cfab6f72d1
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348347B2

Reaction notes

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