Potassium tert-butoxide → HCID 57687394, compound

HRID 559058Notes

Reaction equation

CC(C)([O-])C.[K+].[CH2:7]([O:9][C:10](=[O:29])[C:11]([C:17](=[O:28])[C:18]1[C:23](F)=[C:22]([F:25])[CH:21]=[C:20]([F:26])[C:19]=1[F:27])=[CH:12][NH:13][CH:14]1[CH2:16][CH2:15]1)[CH3:8]>C1COCC1.O1CCOCC1>[CH2:7]([O:9][C:10]([C:11]1[C:17](=[O:28])[C:18]2[C:23](=[C:22]([F:25])[CH:21]=[C:20]([F:26])[C:19]=2[F:27])[N:13]([CH:14]2[CH2:16][CH2:15]2)[CH:12]=1)=[O:29])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium tert-butoxide (2.36 g, 21 mmol) was slowly added to a stirred solution of example 1b (6.62 g, 20 mmol) in 1:1 THF/dioxane (60 mL) at 0° C. The reaction mixture was stirred at 0° C. for 5 h. The precipitate was collected by filtration to give 5.22 g (79%) of clean desired product as a beige solid. The filtrate contained product contaminated with some starting material and was concentrated in vacuo. The residue (1.3 g) was treated by potassium tert-butoxide (350 mg, 3.12 mmol) in 1:1 THF/dioxane (60 mL) for 18 h. Purification by silica gel chromatography gave an additional 1.1 g (18%) of the title compound as a beige solid. 1H NMR (400 MHz, DMSO-d6): δ 8.41 (s, 1H), 8.09-8.19 (m, 1H), 4.21 (q, 211, J=7.2 Hz), 3.88-3.97 (m, 1H), 1.27 (t, 3H, J=7.2 Hz), 1.08-1.14 (m, 4H). MS (ES) [m+H] calc'd for C15H12F3NO3, 312; found 312.

Workup

filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-6a3240a8816845f7b959ef46e2519a5e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063066B2

Reaction notes

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