Lithium Hydroxide → 4-(Biphenyl-4-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid

HRID 1070412Notes

Reaction equation

HRID 1070412 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:8]=[CH:9][C:10]=1[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=[O:13])=[O:4].[Li+].[OH-]>C1COCC1>[C:19]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:21][C:16]([CH2:15][O:14][C:12]([NH:11][C:10]2[CH:9]=[CH:8][C:7]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:6][C:5]=2[C:3]([OH:4])=[O:2])=[O:13])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 696869824-(Biphenyl-4-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 223962834-(Biphenyl-4-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acidYield 63.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(biphenyl-4-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid methyl ester (0.51 g, 1.179 mmol) in THF (5 mL) was added at room temperature 1.0 M LiOH (2.42 mL, 2.42 mmol) 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 with ethyl acetate. The extract was washed with water, then brine, and dried over magnesium sulfate, concentrated to dryness and purified by chromatography to yield 0.317 g of 4-(biphenyl-4-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid 601, mp: 234.5-235.6° C.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthe product was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialbrine, and dried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-c4fd0d99796b433796a834725d1d07ec
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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