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 494618Notes

Reaction equation

HRID 494618 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, 1H) 0.65 (d, J=6.62 Hz, 3H) 0.67 (m, 3H) 0.76 (m, 1H) 1.27 (m, 1H) 1.34 (s, 3H) 1.69 (m, 1H) 2.11 (m, 1H) 7.26 (m, 4H) 7.43 (m, 2H) 7.64 (m, 2H) 7.75 (dd, J=8.46, 1.84 Hz, 1H) 8.03 (m, 4H) 8.38 (s, 1H) 10.54 (s, 1H) 15.37 (s, 1H). 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-11aca80b53f4462bb4bd1957a92c84d5
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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