1-(Mercaptomethyl)cyclopropaneacetic acid → Montelukast

HRID 458223

Reaction equation

HRID 458223 reaction equation
[SH:1][CH2:2][C:3]1([CH2:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4]1.[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][C:17]([CH:21]=[CH:22][C:23]3[CH:24]=[C:25]([C@@H:29](OS(C)(=O)=O)[CH2:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[C:38]([OH:41])([CH3:40])[CH3:39])[CH:26]=[CH:27][CH:28]=3)=[N:18]2)=[CH:13][CH:12]=1>>[CH3:40][C:38]([OH:41])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][CH2:30][C@@H:29]([S:1][CH2:2][C:3]1([CH2:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4]1)[C:25]1[CH:26]=[CH:27][CH:28]=[C:23](/[CH:22]=[CH:21]/[C:17]2[CH:16]=[CH:15][C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:20][C:19]=3[N:18]=2)[CH:24]=1)[CH3:39]

Participants

3

Reactant 2

HCID 97938251-(Mercaptomethyl)cyclopropaneacetic acidHCID 544844832-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-methanesulfonyloxypropyl)phenyl)-2-propanol

Product 1

HCID 5281040Montelukast

Procedure

In U.S. Pat. No. 5,614,632, montelukast is prepared by condensing 1-(mercaptomethyl)cyclopropaneacetic acid then condensation with 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-methanesulfonyloxypropyl)phenyl)-2-propanol compound to afford Montelukast. It is further converted to its corresponding sodium salt via dicyclohexyl amine salt.

Sources & evidence

ORD record
ord-0716dbb845534c8e803484927cb7cd71
Source dataset
uspto-grants-2007_03
Patent number
US07189853B2

Linked notes

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