Sodium hydride → N-(3,4-dichlorophenyl)glycine Iso-butyl Ester

HRID 133333

Reaction equation

HRID 133333 reaction equation
C(NC1C=CC=CC=1)(OC(C)(C)C)=O.[H-].[Na+].BrCC(OCC(C)C)=O.[CH2:26]([O:30][C:31](=[O:49])[CH2:32][N:33](C(OC(C)(C)C)=O)[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=1)[CH:27]([CH3:29])[CH3:28]>C1COCC1>[CH2:26]([O:30][C:31](=[O:49])[CH2:32][NH:33][C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=1)[CH:27]([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 137930t-Butyl carbanilateHCID 5219062-Methylpropyl 2-bromoacetateHCID 54479293N-BOC N-(3,4-dichlorophenyl)glycine iso-butyl ester

Product 1

HCID 9925559N-(3,4-dichlorophenyl)glycine Iso-butyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dichloroaniline (Aldrich) was treated with di-tert-butyl dicarbonate (Aldrich) using conventional procedures to produce the N-BOC aniline. The N-BOC aniline was treated with sodium hydride in THF and then with isobutyl 2-bromoacetate (from Example AD above) to produce the N-BOC N-(3,4-dichlorophenyl)glycine iso-butyl ester. The BOC group was then removed using General Procedure AN above to afford the title compound. The reaction was monitored by tlc on silica gel (Rf=0.78 in 50% EtOAc/hexanes) and purification was by preparative plate chromatography (silica gel using 50% EtOAc/hexanes as the eluant).

Workup

  1. customThe BOC group was then removed

Sources & evidence

ORD record
ord-b8d0a5b444d24e569be2cb70f7778e8b
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Linked notes

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