Potassium tert-butoxide → HCID 67235046, compound

HRID 2368723Notes

Reaction equation

C([O:3][C:4]([C:6]1[S:7][C:8]([Br:30])=[CH:9][C:10]=1[CH2:11][N:12]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[O:28][CH3:29])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)C.CC(C)([O-])C.[K+]>C1COCC1>[CH2:17]([O:16][C:14]([CH:13]1[N:12]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[CH2:11][C:10]2[CH:9]=[C:8]([Br:30])[S:7][C:6]=2[C:4]1=[O:3])=[O:15])[CH3:18]

Participants

Conditions

Temperature: -15 °C

Procedure

5-Bromo-3-{[(2,4-dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-thiophene-2-carboxylic acid ethyl ester (example 21.b, 7.0 g, 14.1 mmol) was dissolved in 140 mL of anhydrous THF and cooled to −15° C. in a brine dry ice bath. A solution of 30 mL of 1.0 M potassium tert-butoxide in THF was added slowly to cold solution, and the reaction mixture was stirred at −15° C. for 30 min. and then at room temperature for 2 hours. The reaction was quenched with 29 mL of 1N HCl. and 400 mL ammonium chloride, and extracted twice with 300 mL ethyl acetate. The organic fractions were washed with brine, dried over anhydrous sodium sulfate and concentrated to 5.67 g of a tan viscous oil: MS: (+) m/z 453.6, 455.5 (M+1, 79Br/81Br)

Workup

waitat room temperature for 2 hours
customThe reaction was quenched with 29 mL of 1N HCl
extractionand 400 mL ammonium chloride, and extracted twice with 300 mL ethyl acetate
washThe organic fractions were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated to 5.67 g of a tan viscous oil

Sources & evidence

ORD record: ord-d8bdbbd43aa747d48586eb2adfe259f9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703795B2

Reaction notes

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