Sodium Hydroxide → Sodium (4r)-2-{7-[(ethylsulfonyl)amino]-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl}-4-methyl-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-1-olate

HRID 2224936Notes

Reaction equation

HRID 2224936 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][S:30]([CH2:33][CH3:34])(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:36])(=[O:35])[N:20]=1.[OH-].[Na+:38]>O>[CH2:33]([S: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:36])(=[O:35])[C:22]=2[CH:28]=1)(=[O:31])=[O:32])[CH3:34].[Na+:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136384653n-{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}ethanesulfonamide

Product 1

HCID 131726898Sodium (4r)-2-{7-[(ethylsulfonyl)amino]-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl}-4-methyl-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-1-olateYield 87.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 102A (70.4 mg, 0.132 mmol) and 0.998 M sodium hydroxide (0.133 mL, 0.132 mmol) in 3 mL water was stirred at rt for 16 h. The reaction mixture was concentrated in vacuo to give the title compound (64 mg, 87% yield). 1H NMR (300 MHz, DMSO-d6) δ 0.46 m, 1 H) 0.68 (d, J=6.62 Hz, 3 H) 0.70 (d, J=6.62 Hz, 3 H) 0.79 m, 1 H) 1.19 (t, J=7.35 Hz, 3 H) 1.29 m, 1 H) 1.38 (s, 3 H) 1.72 m, 1 H) 2.15 (m, 1 H) 3.02 m, 2 H) 7.23 (d, J=7.72 Hz, 1 H) 7.31 m, 2 H) 7.44 m, 3 H) 8.04 (d, J=7.35 Hz, 1 H) 9.96 (s, 1 H) 15.43 (s, 1 H). MS (ESI+) m/z 532.0 (M+H—Na)+, 549.0 (M−Na+NH4)+, (ESI−) m/z 530.0 (M−H—Na)−.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-2c97f4d4ff464112836318a6ce03fc17
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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