Lithium hydroxide, monohydrate → (7-Methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1lambda6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid

HRID 421509Notes

Reaction equation

C([O:3][C:4](=[O:22])[CH2:5][C:6]1[NH:11][C:10]2[S:12][CH:13]=[C:14]([CH2:15][O:16][CH2:17][O:18][CH3:19])[C:9]=2[S:8](=[O:21])(=[O:20])[N:7]=1)C.O.[OH-].[Li+]>O1CCCC1.O>[CH3:19][O:18][CH2:17][O:16][CH2:15][C:14]1[C:9]2[S:8](=[O:21])(=[O:20])[N:7]=[C:6]([CH2:5][C:4]([OH:22])=[O:3])[NH:11][C:10]=2[S:12][CH:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (7-methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester (0.54 g, 1.55 mmol) in tetrahydrofuran (5 mL) and water (5 mL) was added lithium hydroxide monohydrate (0.33 g, 7.75 mmol). The reaction was stirred at 25° C. for 1 h before it was cooled to 0° C. The reaction was quenched via the addition of 6.0 M aqueous hydrochloric acid solution until a pH of 1-2 was reached. The resulting mixture was extracted with ethyl acetate (3×10 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the crude product, (7-methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid (0.39 g, 1.21 mmol, 78%), which was used in the next step without further purification.

Workup

temperaturewas cooled to 0° C
customThe reaction was quenched via the addition of 6.0 M aqueous hydrochloric acid solution until a pH of 1-2
extractionThe resulting mixture was extracted with ethyl acetate (3×10 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0326fe88d2514b2b93f020ab28b785ad
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097613B2

Reaction notes

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