Hydrochloric Acid → (1r)-1-(3,3-Dimethylbutyl)-4-hydroxy-3-[7-(hydroxymethyl)-1,1-dioxido-4h-thieno[2,3-e][1,2,4]thiadiazin-3-yl]-1-methylnaphthalen-2(1h)-one

HRID 494670Notes

Reaction equation

HRID 494670 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[CH2:3][CH2:4][C@:5]1([CH3:33])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[S:22][CH:23]=[C:24]([CH2:25][O:26]COC)[C:19]=3[S:18](=[O:31])(=[O:30])[N:17]=2)[C:6]1=[O:32].Cl>O1CCOCC1>[CH3:1][C:2]([CH3:35])([CH3:34])[CH2:3][CH2:4][C@:5]1([CH3:33])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[S:22][CH:23]=[C:24]([CH2:25][OH:26])[C:19]=3[S:18](=[O:31])(=[O:30])[N:17]=2)[C:6]1=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 135903311(1R)-1-(3,3-dimethylbutyl)-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}-1-methylnaphthalen-2(1H)-one

Product 1

HCID 135953291(1r)-1-(3,3-Dimethylbutyl)-4-hydroxy-3-[7-(hydroxymethyl)-1,1-dioxido-4h-thieno[2,3-e][1,2,4]thiadiazin-3-yl]-1-methylnaphthalen-2(1h)-oneYield 113.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of Example 184 (2.84 g, 5.5 mmol) in 20 mL of dioxane was cooled to 0° C., treated with 60 mL of 4N HCl in dioxane, allowed to warm to room temp, stirred for 2 hrs, and concentrated in vacuo to afford the title compound (2.96 g, 100% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.39 (m, 1H), 0.72 (s, 9H), 0.82 (m, 1H), 1.56 (s, 3H), 2.03 (m, 1H), 2.22 (m, 1H), 4.61 (s, 2H), 7.26 (s, 1H), 7.52 (m, 1H), 7.74 (d, J=4.0 Hz, 2H), 8.13 (d, J=7.7 Hz, 1H), 14.07 (s, 1H); MS (APCI+) m/z 475 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f126172ebe243ae845b9bba7d7b7d4f
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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