Tetrahydrofuran → 2-Amino-3'-(tert-butoxycarbonylaminomethyl)benzophenone

HRID 275857Notes

Reaction equation

HRID 275857 reaction equation
O1CCCC1.CN(OC)[C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15].[C:19]([O:23][C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30](Br)[CH:29]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C([Li])CCC>C(OC(=O)C)C.O.CCCCCC>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]([C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:27][NH:26][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[CH:33]=1)=[O:16]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 11033439tert-Butyl 3-bromobenzylcarbamateHCID 110522422-amino-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 183153742-Amino-3'-(tert-butoxycarbonylaminomethyl)benzophenone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran (30 ml) solution of N-methyl-N-methyloxy-2-aminobenzamide (2.70 g) and N-tert-butoxycarbonyl-3-bromobenzylamine (2.86 g) was cooled to −78° C. To the solution was gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (31 ml). To the mixture were then added water (70 ml) and acetic acid ethyl ester (70 ml). The organic layer was washed with water and dried over anhydrous MgSO4. The solvent was then distilled off. The residual oily compound was purified by means of a silica gel column chromatography to give 2-amino-3′-(tert-butoxycarbonylaminomethyl)benzophenone as a yellow oily product (1.2 g).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. distillationThe solvent was then distilled off
  4. customThe residual oily compound was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-6f193324f3ad43929deabd9c727960a6
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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