Tetrahydrofuran → 2'-(((2,4'-Dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

HRID 2167129Notes

Reaction equation

HRID 2167129 reaction equation
[OH-].[Na+].C1COCC1.[Cl:8][C:9]1[CH:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35]C)=[O:34])=[CH:29][CH:28]=2)[CH:12]=[CH:11][C:10]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=1[CH3:44]>CO>[Cl:8][C:9]1[CH:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[C:27]2[CH:28]=[CH:29][C:30]([C:33]([OH:35])=[O:34])=[CH:31][CH:32]=2)[CH:12]=[CH:11][C:10]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=1[CH3:44]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71060181Methyl 2'-(((2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 710598532'-(((2,4'-Dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3M aqueous solution of NaOH (0.6 mL, 1.8 mmol) was added to a THF (3 mL) and MeOH (1.5 mL) solution of methyl 2′-(((2,4′-dichloro-2′-methyl-[1,1′-biphenyl]-4-yl)amino)methyl)-5′-(trifluoromethyl)-[1,1′-biphenyl]-4-carboxylate (326 mg, 0.6 mmol) and the resulting homogeneous mixture was stirred at room temperature. After 16 h the resulting mixture was concentrated in vacuo, suspended in water, and acidified with 2 M HCl. The resulting precipitate was filtered off, dried in vacuo, and purified via HPLC to yield the title compound.

Workup

  1. concentrationAfter 16 h the resulting mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. customdried in vacuo
  4. custompurified via HPLC

Sources & evidence

ORD record
ord-a85a90688e904412b00847a52ddea591
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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