Tetrahydrofuran → 2-Amino-4'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone

HRID 275849Notes

Reaction equation

HRID 275849 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][C:29]1[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=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:32]1[CH:31]=[CH:30][C:29]([CH2:28][NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[CH:34][CH:33]=1)=[O:17]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 12453839tert-butyl N-[(4-bromophenyl)methyl]carbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 183153642-Amino-4'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenoneYield 25%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran (30 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (3.21 g) and N-tert-butoxycarbonyl-4-bromobenzylamine (2.86 g) was cooled to −78° C. To the solution kas gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (31 ml). To the mixture were then added water (100 ml) and acetic acid ethyl ester (100 ml). The organic layer was washed with water and dried over anhydrous MgSO4. The solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography. followed by crystallization. The crystals were collected to give 2-amino-4′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (0.9 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 then distilled off
  4. customthe residue was purified by means of a silica gel column chromatography
  5. customfollowed by crystallization
  6. customThe crystals were collected

Sources & evidence

ORD record
ord-79d384d4b9734a568bbbe4fa09c91c97
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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