Hydrochloric Acid → (2'-{[Ethyl-(2-phenylsulfanyl-acetyl)-amino]-methyl}-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

HRID 1810289Notes

Reaction equation

HRID 1810289 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][N:25]([CH2:36][CH3:37])[C:26](=[O:35])[CH2:27][S:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)C.[Li+].[OH-].Cl>C1COCC1>[CH2:36]([N:25]([CH2:24][C:15]1[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:14]=1[C:8]1[C:9]([O:12][CH3:13])=[CH:10][CH:11]=[C:6]([CH2:5][C:4]([OH:38])=[O:3])[CH:7]=1)[C:26](=[O:35])[CH2:27][S:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66608549(2'-{[Ethyl-(2-phenylsulfanyl-acetyl)-amino]-methyl}-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 66607490(2'-{[Ethyl-(2-phenylsulfanyl-acetyl)-amino]-methyl}-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2′-{[Ethyl-(2-phenylsulfanyl-acetyl)-amino]-methyl}-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.291 g, 0.53 mmol) in THF (3 mL) was treated with 1N aqueous LiOH (3 mL) at room temperature overnight. The mixture was acidified with 1N aqueous HCl and extracted three times with EtOAc. The combined organic layers were dried and concentrated, and the residue was purified by silica gel chromatography (30-70% EtOAc in hexanes) to give the title compound. M+H is 518.

Workup

  1. extractionextracted three times with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customthe residue was purified by silica gel chromatography (30-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cbb0bd5f1ded45acbb20025bf81df1d1
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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