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 494583Notes

Reaction equation

HRID 494583 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, 1H) 0.69 (m, 6H) 0.80 (m, 1H) 1.27 (m, 1H) 1.37 (m, 3H) 1.72 (m, 1H) 2.06 (m, 3H) 2.15 (m, 1H) 7.23 (m, 1H) 7.32 (m, 1H) 7.46 (m, 2H) 7.65 (m, 1H) 8.03 (m, 2H) 10.13 (m, 1H) 15.44 (m, 1H). MS (ESI−) m/z 480 (M−H)−.

Sources & evidence

ORD record
ord-844f57e7882d4149ab99641317f04fd4
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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