Sodium Hydroxide → HCID 11014609, compound

HRID 2270348Notes

Reaction equation

HRID 2270348 reaction equation
C([O:3][C:4](=[O:29])[C:5]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])([CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])C.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([C:41]([CH2:50][C:51]2[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=2)([CH2:45][CH:46]=[C:47]([CH3:49])[CH3:48])[C:42]([OH:44])=O)(=[O:40])=[O:39])=[CH:34][CH:33]=1.[OH-:57].[Na+]>CO>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([S:18]([C:5]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)([CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[C:4]([OH:29])=[O:3])(=[O:20])=[O:19])=[CH:22][CH:23]=1.[OH:57][NH:14][C:42](=[O:44])[C:41]([S:38]([C:35]1[CH:34]=[CH:33][C:32]([O:31][CH3:30])=[CH:37][CH:36]=1)(=[O:40])=[O:39])([CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1)[CH2:45][CH:46]=[C:47]([CH3:48])[CH3:49]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 10884248HCID 10884248, compoundHCID 11014609HCID 11014609, compound

Product 2

HCID 11014609HCID 11014609, compoundHCID 17897285HCID 17897285, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4Methoxy-benzenesulfonyl)-5-methyl-2-pyridin-3-ylmethyl-hex-4 enoic acid was prepared starting from 2-(4-methoxy-benzenesulfonyl)-5-methyl-2-pyridin-3-ylmethyl-hex-4-enoic acid ethyl ester (4.0 g, 9.5 mmol) dissolved in methanol (50 ml) and 10 N NaOH (30 ml). The resulting reaction mixture was worked up as outlined in Example 9. Yield 3.2 g, 87%; ivory solid; mp 117-119° C.; MS: 390 (M+H)+. Starting from 2-(4-methoxy-benzenesulfonyl)-5-methyl-2-pyridin-3-ylmethyl-hex-4-enoic acid (2.1 g, 5.4 mmol) and following the procedure as outlined in Example 1, 1.82 g of 2-(4-methoxy-benzenesulfonyl)-5-methyl-2-pyridin-3-ylmethyl-hex-4-enoic acid hydroxyamide was isolated as a colorless solid. Yield: 82%; mp 89-92° C.; MS: 405 (M+H)+; 1H NMR (300 MHz, CDCl3): δ1.63 (s, 3H), 1.76 (s, 3H), 2.62-2.78 (m, 2H), 3.3 (d, J=4.0 Hz, 1H), 3.63 (d, J=4.0 Hz, 1H), 3.82 (s, 3H), 5.26 (m, 1H), 7.12-7.88 (m, 6H), 8.27-8.33 (m. 2H).

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-6e9361a016554ec8898a328cbeddcd63
Source dataset
uspto-grants-2001_12
Patent number
US06331563B1

Reaction notes

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