Acetate → HCID 60878511, compound

HRID 850384Notes

Reaction equation

HRID 850384 reaction equation
[ClH:1].NO.[C:4]1([OH:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(=O)C.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[OH-].[Li+].[CH2:24]([NH2:26])C.C1(N)CC1>C(=O)([O-])[O-].[Na+].[Na+].[Rh]>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:10][C:4]1[CH:9]=[CH:8][C:7]([Cl:1])=[CH:6][C:5]=1[CH2:24][NH2:26])[CH3:21]

Participants

10

Reactant 7

HCID 175AcetateHCID 996PhenolHCID 3939Lithium HydroxideHCID 6341EthylamineHCID 7748Ethyl bromoacetateHCID 69828CyclopropylamineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 60878511HCID 60878511, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 10340Sodium CarbonateSolvent

Procedure

4-Chlorosalicaldehyde is condensed with hydroxylamine hydrochloride in ethanolic aqueous sodium carbonate solution in Step A. The oxime is reduced by hydrogenation over a catalyst such as rhodium and the amine is protected as its BOC derivative under standard conditions. The phenol is alkylated in Step D with an acetate equivalent such as ethyl bromoacetate and the resulting ester is hydrolysed with lithium hydroxide. The product carboxylic acid is coupled to an amine such as ethylamine or cyclopropylamine in Step F, and the BOC group is removed by strong acid such as TFA in Step G. ##STR13##

Workup

  1. customthe BOC group is removed by strong acid such as TFA in Step G

Sources & evidence

ORD record
ord-1e5c7233a7d34343b7121fb36909d6f2
Source dataset
uspto-grants-2000_01
Patent number
US06017934

Reaction notes

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