Hydrochloric Acid → 4-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid

HRID 1070394Notes

Reaction equation

HRID 1070394 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]=[CH:9][C:10]=1[NH:11][C:12]([O:14][CH2:15][C:16]1[O:17][C:18]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][C:19]=2[CH:20]=1)=[O:13])=[O:4].O.[OH-].[Li+].Cl>C1COCC1.CO.O>[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:10]4[CH:9]=[CH:8][C:7]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:6][C:5]=4[C:3]([OH:4])=[O:2])=[O:13])=[CH:20][C:19]=3[CH:21]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 696873694-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 101396444-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acidYield 53.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid methyl ester (1.04 g, 2.17 mmol) in THF (35 mL), methyl alcohol (4.5 mL) and water (5.5 mL) was added lithium hydroxide monohydrate (0.19 g, 4.47 mmol). The mixture was stirred for 3 h, and 1N HCl was added to adjust the pH to 2. The solvents were removed in vacuo and the resulting suspension was filtered. Recrystallisation of the white crude solid gave 0.54 g of 4-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid 10, mp: 225.9-226.2° C.

Workup

  1. customThe solvents were removed in vacuo
  2. filtrationthe resulting suspension was filtered
  3. customRecrystallisation of the white crude solid

Sources & evidence

ORD record
ord-9b12a7f295e84bd1b84a4b7cdd5c1010
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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