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

HRID 2224938Notes

Reaction equation

HRID 2224938 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]([C:33]3[CH:42]=[CH:41][C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH:34]=3)(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:44])(=[O:43])[N:20]=1.[OH-].[Na+:46]>O>[CH3:17][C@@:5]1([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O-:1])=[C:3]([C:19]2[NH:24][C:23]3[CH:25]=[CH:26][C:27]([NH:29][S:30]([C:33]4[CH:42]=[CH:41][C:40]5[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=5)[CH:34]=4)(=[O:32])=[O:31])=[CH:28][C:22]=3[S:21](=[O:44])(=[O:43])[N:20]=2)[C:4]1=[O:18].[Na+:46]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136384730n-{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}naphthalene-2-sulfonamide

Product 1

HCID 131726899Sodium (4r)-4-methyl-4-(3-methylbutyl)-2-{7-[(2-naphthylsulfonyl)amino]-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl}-3-oxo-3,4-dihydronaphthalen-1-olateYield 95.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 103A (10.0 mg, 0.016 mmol) and 0.998 M sodium hydroxide (0.016 mL, 0.016 mmol) in water (1 mL) was stirred at rt for 16 h. The reaction mixture was concentrated in vacuo to give the title compound (10.0 mg, quant. yield). 1H NMR (300 MHz, DMSO-d6) δ 0.40 m, 1 H) 0.65 (d, J=6.62 Hz, 3 H) 0.67 m, 3 H) 0.76 (m, 1 H) 1.27 m, 1 H) 1.34 (s, 3 H) 1.69 m, 1 H) 2.11 m, 1 H) 7.26 m, 4 H) 7.43 (m, 2 H) 7.64 m, 2 H) 7.75 (dd, J=8.46, 1.84 Hz, 1 H) 8.03 m, 4 H) 8.38 (s, 1 H) 10.54 (s, 1 H) 15.37 (s, 1 H). MS (ESI+) m/z 630.0 (M+H—Na)+, 647.1.0 (M−Na+NH4)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-136d8482a1ae4e3c9c3de43c621597e2
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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