Hydrochloric Acid → HCID 18551841, compound

HRID 1266709Notes

Reaction equation

HRID 1266709 reaction equation
C([O:3][C:4](=[O:28])[CH:5]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1)[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[C:8]([O:15][CH2:16][CH3:17])[C:7]=1[F:18])C.[Li+].[OH-].Cl.C(OCC)(=O)C>C1COCC1>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([NH:19][CH:5]([C:6]2[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[C:8]([O:15][CH2:16][CH3:17])[C:7]=2[F:18])[C:4]([OH:28])=[O:3])=[CH:21][CH:22]=1)#[N:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 70004790HCID 70004790, compound

Product 1

HCID 18551841HCID 18551841, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (RS)-(4-cyano-phenylamino)-(3,5-diethoxy-2-fluoro-phenyl)-acetic acid ethyl ester (1.02 g) described in example 2.2 was dissolved in THF. 1 M LiOH (3.96 ml) was added and the mixture was stirred for 2 h at room temperature. 1 M HCl (4 ml) was added. The product was isolated by extraction with ethyl acetate to give 970 mg of (RS)-(4-cyano-phenylamino)-(3,5-diethoxy-2-fluoro-phenyl)-acetic acid which was used for the next step without further purification. MS: 357 ([M−H]−)

Sources & evidence

ORD record
ord-d7cc0209a6c742a8a4827482067a9d41
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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