Sodium Hydroxide → Sodium (4R)-2-[7-(acetylamino)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-methyl-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-1-olate

HRID 2224904Notes

Reaction equation

HRID 2224904 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@:5]([CH3:17])([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([NH:29][C:30](=[O:32])[CH3:31])=[CH:28][C:22]=2[S:21](=[O:34])(=[O:33])[N:20]=1.[OH-].[Na+:36]>O>[C:30]([NH:29][C:27]1[CH:26]=[CH:25][C:23]2[NH:24][C:19]([C:3]3[C:4](=[O:18])[C@:5]([CH3:17])([CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:2]=3[O-:1])=[N:20][S:21](=[O:33])(=[O:34])[C:22]=2[CH:28]=1)(=[O:32])[CH3:31].[Na+:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135409606N-{3-[(4R)-1-hydroxy-4-methyl-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}acetamide

Product 1

HCID 86598022Sodium (4R)-2-[7-(acetylamino)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-methyl-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-1-olateYield 993%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of the product of Example 44A (0.046 g) in water (1 mL) was treated with 0.997N sodium hydroxide solution (0.090 mL, 0.090 mmol) and stirred at 25° C. for 1 hour. The solution was lyophilized to give the title compound (0.45 g, 99%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.45 m, 1 H) 0.69 m, 6 H) 0.80 m, 1 H) 1.27 m, 1 H) 1.37 (m, 3H) 1.72 m, 1 H) 2.06 m, 3 H) 2.15 m, 1 H) 7.23 m, 1 H) 7.32 m, 1 H) 7.46 (m, 2 H) 7.65 m, 1 H) 8.03 m, 2 H) 10.13 m, 1 H) 15.44 m, 1 H). MS (ESI−) m/z 480 (M−H)−.

Sources & evidence

ORD record
ord-33ef93cb90244efb89461e399b212ed9
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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