Methanol → 4-[7-(2-Ethylbutylcarbamoyl)naphth-1-ylmethyl]-3-methoxybenzoic acid

HRID 2371799Notes

Reaction equation

HRID 2371799 reaction equation
O.[OH-].[Li+].[CH2:4]([CH:6]([CH2:34][CH3:35])[CH2:7][NH:8][C:9]([C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][CH:17]=[C:18]2[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[CH:13][CH:12]=1)=[O:10])[CH3:5].CO.O1CCCC1>O>[CH2:34]([CH:6]([CH2:4][CH3:5])[CH2:7][NH:8][C:9]([C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][CH:17]=[C:18]2[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[CH:13][CH:12]=1)=[O:10])[CH3:35]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 19906363Methyl 4-(7-(2-ethylbutylcarbamoyl)naphth-1-ylmethyl)-3-methoxybenzoate

Product 1

HCID 199063694-[7-(2-Ethylbutylcarbamoyl)naphth-1-ylmethyl]-3-methoxybenzoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of lithium hydroxide monohydrate (150 mg) in water (4 ml) was added to a solution of methyl 4-(7-(2-ethylbutylcarbamoyl)naphth-1-ylmethyl)-3-methoxybenzoate (310 mg) in 1:1 methanol:tetrahydrofuran (15 ml). The mixture was stirred for 18 h. After most of the solvent was evaporated, water (7 ml) was added. The mixture was acidified with 1N hydrochloric acid and the precipitate was filtered, triturated with 25 ml of 10:1 ether:methanol, ground to a powder and vacuum dried at 100° C for 12 h to give 4-[7-(2-ethylbutylcarbamoyl)naphth-1-ylmethyl]-3-methoxybenzoic acid (221 mg, 74%) as a colorless solid; mp 198.0°-199.0° C.

Workup

  1. customAfter most of the solvent was evaporated
  2. additionwater (7 ml) was added
  3. filtrationthe precipitate was filtered
  4. customtriturated with 25 ml of 10:1 ether
  5. dry with materialmethanol, ground to a powder and vacuum dried at 100° C for 12 h

Sources & evidence

ORD record
ord-5e8943b8fa9e42aea30f3b1eea7ac6a7
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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