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

HRID 1369774Notes

Reaction equation

HRID 1369774 reaction equation
[H-].[Na+].BrCC(OCC(C)C)=O.[CH2:12]([O:16][C:17](=[O:35])[CH2:18][N:19](C(OC(C)(C)C)=O)[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[CH:13]([CH3:15])[CH3:14]>C1COCC1>[CH2:12]([O:16][C:17](=[O:35])[CH2:18][NH:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 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 iso-butyl 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-486e917e99a046d7bbcb7bacd641dc0e
Source dataset
uspto-grants-2003_06
Patent number
US06579867B2

Reaction notes

Loading…