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

HRID 2167136Notes

Reaction equation

HRID 2167136 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][C:28]=2[CH3:37])[CH:12]=[CH:11][C:10]=1[C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][C:39]=1[CH3:45]>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:32]=[CH:31][C:30]([C:33]([OH:35])=[O:34])=[CH:29][C:28]=2[CH3:37])[CH:12]=[CH:11][C:10]=1[C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][C:39]=1[CH3:45]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71060183Methyl 2'-(((2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-2-methyl-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 710601112'-(((2,4'-Dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-2-methyl-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3M aqueous solution of NaOH (0.26 mL, 0.79 mmol) was added to a THF (2 mL) and MeOH (1 mL) solution of methyl 2′-(((2,4′-dichloro-2′-methyl-[1,1′-biphenyl]-4-yl)amino)methyl)-2-methyl-5′-(trifluoromethyl)-[1,1′-biphenyl]-4-carboxylate (340 mg, 0.61 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 the resulting residue was used in the next step without further purification.

Workup

  1. concentrationAfter 16 h the resulting mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. customdried in vacuo
  4. customthe resulting residue was used in the next step without further purification

Sources & evidence

ORD record
ord-06ebc197953c48c79a3136473163d008
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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