Hexane → 2-Amino-3'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone

HRID 275828Notes

Reaction equation

HRID 275828 reaction equation
CN(OC)[C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH2:11].[C:15]([O:19][C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](Br)[CH:25]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CCCCCC.C([Li])CCC>O1CCCC1.C(OC(=O)C)C.O>[NH2:11][C:5]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=1[C:3]([C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:23][NH:22][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH:29]=1)=[O:12]

Participants

8

Reactant 4

HCID 8058HexaneHCID 11033439tert-Butyl 3-bromobenzylcarbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 183153602-Amino-3'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenoneYield 45.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (24.8 g) and N-tert-butoxycarbonyl-3-bromobenzylamine (22.0 g) in tetrahydrofuran (300 ml) was cooled to −78° C. To the solution was gradually added dropwise a hexane solution (1.6 mol./L)(240 ml) of n-butyl lithium. To the mixture were then added water (300 ml) and acetic acid ethyl ester (300 ml). The organic layer was washed with water, which was dried over anhydrous MgSO4, then the solvent was distilled off. To the residual oily compound was added hexane (400 ml) to cause crystallization. The crystalline product was collected by filtration to give 2-amino-3′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (12.5 g) as pale yellow crystals.

Workup

  1. washThe organic layer was washed with water, which
  2. dry with materialwas dried over anhydrous MgSO4
  3. distillationthe solvent was distilled off
  4. additionTo the residual oily compound was added hexane (400 ml)
  5. customcrystallization
  6. filtrationThe crystalline product was collected by filtration

Sources & evidence

ORD record
ord-04c1ec66843242fd9899c0a398ee3a51
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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