Sodium Hydroxide → 2-{[1-(4-Bromo-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid

HRID 2062050Notes

Reaction equation

HRID 2062050 reaction equation
C[O:2][C:3](=[O:29])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)=[O:9])([CH3:6])[CH3:5].[OH-].[Na+]>C1COCC1>[Br:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][O:20][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][C:10]=2[C:8]([NH:7][C:4]([CH3:5])([CH3:6])[C:3]([OH:29])=[O:2])=[O:9])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 667011992-{[1-(4-Bromo-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester

Product 1

HCID 115612932-{[1-(4-Bromo-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acidYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 96 mg 2-{[1-(4-bromo-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester in 1 ml dry THF was treated with 0.2 ml of 2 M aqueous sodium hydroxide. After 4 h at 60° C. the reaction was concentrated, the residue was taken up in 3 ml of water, treated with 2 M hydrochloric acid, and the resulting precipitate was collected by filtration and purified by RP-HPLC to yield 70 mg 2-{[1-(4-bromo-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid.

Workup

  1. concentrationAfter 4 h at 60° C. the reaction was concentrated
  2. additiontreated with 2 M hydrochloric acid
  3. filtrationthe resulting precipitate was collected by filtration
  4. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-64ab2df9a38d4d1a9d828177081810bc
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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