Hexane → 2-Amino-3'-(2-tert-butoxycarbonylaminoethyl)-5-chloro-benzophenone

HRID 275867Notes

Reaction equation

HRID 275867 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(OC)[C:20](=[O:29])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[NH2:28].CCCCCC.C([Li])CCC>O1CCCC1.C(OCC)(=O)C.O>[NH2:28][C:22]1[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=1[C:20]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=1)=[O:29]

Participants

8

Reactant 4

HCID 8058HexaneHCID 18315328Tert-butyl 3-bromophenethylcarbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 183153892-Amino-3'-(2-tert-butoxycarbonylaminoethyl)-5-chloro-benzophenoneYield 70.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-tert-butoxycarbonyl-3-bromophenethylamine (1.7 g) and N-methyl-N-methyloxy-2-amino-5-chloro-benzamide (1.9 g) in tetrahydrofuran (50 ml) was cooled to -70° C. To the solution was added dropwise, while stirring, a hexane solution of n-butyl lithium (1.6 mol/L) (18 ml). To the reaction mixture were added water (100 ml) and ethyl acetate (80 ml). The mixture was shaken. The organic layer was separated, which was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 2-amino-3′-(2-tert-butoxycarbonylaminoethyl)-5-chloro-benzophenone (1.5 g) as a yellow crystalline product. m.p.: 128-129° C.

Workup

  1. additionTo the solution was added dropwise
  2. stirringThe mixture was shaken
  3. customThe organic layer was separated
  4. washwhich was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-52e078ed5ef54f3082b3b1bda7d562bb
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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