Lithium Hydroxide → 5-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid

HRID 1070407Notes

Reaction equation

HRID 1070407 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:8]=[C:9]([NH:11][C:12]([O:14][CH2:15][C:16]2[O:17][C:18]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:21][C:19]=3[CH:20]=2)=[O:13])[CH:10]=1)=[O:4].[Li+].[OH-]>C1COCC1>[C:25]1([C:22]2[CH:23]=[CH:24][C:18]3[O:17][C:16]([CH2:15][O:14][C:12]([NH:11][C:9]4[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[C:7]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH:8]=4)=[O:13])=[CH:20][C:19]=3[CH:21]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 696877795-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic Acid Methyl Ester

Product 1

HCID 223962775-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acidYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid methyl ester (0.125 g, 0.2618 mmol) in THF (2 mL) was added at room temperature 1.0 M LiOH and the mixture was stirred for 3 h. The solvent was evaporated, water was added, followed by 2N HCl to adjust the pH to 1-2, and the product was extracted, washed with water, then brine, and dried over magnesium sulfate and concentrated to dryness. Purification by crystallization gave 0.040 g of 5-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid 401 as a white solid, mp: 235.7-238.9° C.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthe product was extracted
  4. washwashed with water
  5. dry with materialbrine, and dried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customPurification
  8. customby crystallization

Sources & evidence

ORD record
ord-c656394052724a5b89493e707c41298b
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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