Potassium tert-butoxide → HCID 67235046, compound

HRID 1465935Notes

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 UV 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, and 400 mL ammonium chloride
extractionextracted 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-ed1f9bd2f15348b49cdfdf368e300dce
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000006B2

Reaction notes

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