Tetrahydrofuran → 3-(5-(2-(([1,1'-Biphenyl]-4-ylamino)methyl)phenyl)picolinamido)propanoic acid

HRID 405111Notes

Reaction equation

HRID 405111 reaction equation
[OH-].[Na+].C1COCC1.[C:8]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[O:29])=[N:26][CH:27]=2)=[CH:10][CH:9]=1>CO>[C:8]1([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:9]=[CH:10][C:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:29])=[N:26][CH:27]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71059913Ethyl 3-(5-(2-(([1,1'-biphenyl]-4-ylamino)methyl)phenyl)picolinamido)propanoate

Product 1

HCID 710599593-(5-(2-(([1,1'-Biphenyl]-4-ylamino)methyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3M aqueous solution of NaOH (0.1 mL, 0.30 mmol) was added to a THF (1 mL) and MeOH (0.5 mL) solution of ethyl 3-(5-(2-(([1,1′-biphenyl]-4-ylamino)methyl)phenyl)picolinamido)propanoate (73 mg, 0.15 mmol) and the homogeneous mixture was stirred at room temperature. After 3 h the resulting mixture was concentrated in vacuo, suspended in water, and acidified with 2M HCl. The resulting precipitate was filtered off and dried in vacuo to yield the title compound.

Workup

  1. concentrationAfter 3 h the resulting mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-9e1098e776f24271ab8a72311a8c40cc
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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