Tetrahydrofuran → 2-Amino-4'-(2-tert-butoxycarbonylaminoethyl)-5-chlorobenzophenone

HRID 275852Notes

Reaction equation

HRID 275852 reaction equation
O1CCCC1.CN(OC)[C:8](=[O:17])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH2:16].[C:20]([O:24][C:25]([NH:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32](Br)[CH:31]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([Li])CCC>C(OC(=O)C)C.O.CCCCCC>[NH2:16][C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([C:33]1[CH:32]=[CH:31][C:30]([CH2:29][CH2:28][NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[CH:35][CH:34]=1)=[O:17]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 18315328Tert-butyl 3-bromophenethylcarbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 183153782-Amino-4'-(2-tert-butoxycarbonylaminoethyl)-5-chlorobenzophenoneYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran (70 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (6.4 g) and N-tert-butoxycarbonyl-3-bromophenethylamine (6.0 g) was cooled to −78° C., to which was gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (67 ml). To the mixture were then added water (300 ml) and acetic acid ethyl ester (300 ml). The organic layer was washed with water and dried over anhydrous MgSO4, and the solvent was distilled off. The residual oily compound was purified by means of a silica gel column chromatography, followed by recrystallization from hexane to afford 2-amino-4′-(2-tert-butoxycarbonylaminoethyl)-5-chlorobenzophenone (3.97 g) as a pale yellow crystalline product.

Workup

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

Sources & evidence

ORD record
ord-9760d44486f5462d9b746c158417ff9c
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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