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

HRID 1810241Notes

Reaction equation

HRID 1810241 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=2[CH2:19][NH:20][CH2:21][C:22]([O:24]C)=[O:23])=[CH:7][C:6]([CH2:26][C:27]([OH:29])=[O:28])=[CH:5][CH:4]=1.[C:30](Cl)(=[O:32])[CH3:31].C(N(CC)CC)C.[OH-].[Na+].Cl>C(Cl)Cl>[C:30]([N:20]([CH2:19][C:10]1[CH:11]=[C:12]([C:15]([F:17])([F:18])[F:16])[CH:13]=[CH:14][C:9]=1[C:8]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]([CH2:26][C:27]([OH:29])=[O:28])[CH:7]=1)[CH2:21][C:22]([OH:24])=[O:23])(=[O:32])[CH3:31]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 66608325HCID 66608325, compound

Product 1

HCID 66607781{2'-[(Acetyl-carboxymethyl-amino)-methyl]-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{6-Methoxy-2′-[(methoxycarbonylmethyl-amino)-methyl]-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid (0.094 g, 0.23 mmol), acetyl chloride (0.03 mL, 0.46 mmol), and triethylamine (0.08 mL, 0.57 mmol) were combined in CH2Cl2 (1 mL) and stirred at room temperature for 1 hour. Once no starting material was seen by analytical LCMS, aqueous 1N NaOH was added. After stirring at room temperature for 45 minutes, analytical LCMS indicated that both acids had been hydrolyzed to the free acid, and so the mixture was neutralized with aqueous 1N HCl and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound. M+H is 440.

Workup

  1. additionwas added
  2. stirringAfter stirring at room temperature for 45 minutes
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe618412ecc94059b2ae9b258682babc
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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