3-Cyano-2-[3-(2-methoxy-phenyl)-propionylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid 2-acetoxy-ethyl ester → 3-Cyano-2-[3-(2-methoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid 2-hydroxy-ethyl ester

HRID 18686Notes

Reaction equation

HRID 18686 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[C:16]([C:32]#[N:33])=[C:17]([NH:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[S:18][C:12]=2[CH2:11]1)=[O:9])(=O)C>[OH-].[Na+]>[OH:4][CH2:5][CH2:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[C:16]([C:32]#[N:33])=[C:17]([NH:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[S:18][C:12]=2[CH2:11]1)=[O:9]

Participants

3

Reactant 1

HCID 118574343-Cyano-2-[3-(2-methoxy-phenyl)-propionylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid 2-acetoxy-ethyl ester

Product 1

HCID 118574373-Cyano-2-[3-(2-methoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid 2-hydroxy-ethyl ester

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3-Cyano-2-[3-(2-methoxy-phenyl)-propionylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid 2-acetoxy-ethyl ester (Example 31) is stirred in 1N NaOH over night at room temperature. After acidification with aqueous HCl the precipitated product is filtered off and recristalized from ethanol.

Workup

  1. filtrationAfter acidification with aqueous HCl the precipitated product is filtered off

Sources & evidence

ORD record
ord-284a7f1bb14041a2acb5c560ed9b9880
Source dataset
uspto-grants-2010_06
Patent number
US07741488B2

Reaction notes

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