Sodium Hydroxide → 5-Methyl-6-oxoheptanesulfonic acid

HRID 1039017

反応式

HRID 1039017 の反応式
[OH-].[Na+].C(O[C:6]([C:8](C)([C:17](=[O:19])[CH3:18])[CH2:9][CH2:10][CH2:11][CH2:12][S:13]([OH:16])(=[O:15])=[O:14])=O)C>O.CO>[CH3:6][CH:8]([C:17](=[O:19])[CH3:18])[CH2:9][CH2:10][CH2:11][CH2:12][S:13]([OH:16])(=[O:14])=[O:15]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 580840065-Ethyloxycarbonyl-5-methyl-6-oxo-1-heptanesulfonic acid

生成物 1

HCID 579033515-Methyl-6-oxoheptanesulfonic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A solution of 290 mg of NaOH in 3 ml water was added to the mixture of 710 mg (2.53 mmol) of 5-ethyloxycarbonyl-5-methyl-6-oxo-1-heptanesulfonic acid in 15 ml of methanol. The obtained mixture was stirred for 15 hours at 50° C. Methanol was removed by a rotary evaporator, residue was acidified to pH 1 and then solvent was removed until dry to yield 5-methyl-6-oxo-1-heptanesulfonic acid. The product thus obtained (940 mg, 4.5 mmol), 1.02 g (5.4 mmol) of 4-hydrazinobenzenesulfonic acid, and 15 ml of acetic acid was refluxing for 16 hours. The insoluble precipitate was filtered and the filtrate was evaporated. The obtained residue was column purified (RP-18, water) to yield 840 mg of the 2,3-dimethyl-3-(4-sulfobutyl)-3H-5-indolesulfonic acid (IVd). δH (200 MHz, DMSO-d6): 7.66 (1H, s, arom H), 7.6 (1H, d, 8.0 Hz, arom H), 7.4 (1H, d, 7.8 Hz arom H), 2.66 (2H, t, 6.8 Hz, CH2SO3H), 2.32 (3H, s, 2-CH3), 2.10-1.78 (2H, m, CH2), 1.53-1.26 (2H, m, C H2), 1.31 (3H, s, 3-C H3), 0.83-0.41 (2H, m, CH2).

後処理

  1. customMethanol was removed by a rotary evaporator, residue
  2. customsolvent was removed
  3. customuntil dry

出典と根拠

ORDレコード
ord-c10bb7aa0c664b1ca71b6dd770b071af
出典データセット
uspto-grants-2013_10
特許番号
US08552027B2

関連ノート

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