Dimethylformamide → 3,5-dichloro-N-trifluoroacetyl-O-[(2-phenylbenzo[b]fur-7-yl)methyl]-L-tyrosine methyl ester

HRID 1393377Notes

Reaction equation

HRID 1393377 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]1[C:14]2[O:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:17][C:13]=2[CH:12]=[CH:11][CH:10]=1.[CH3:24][O:25][C:26](=[O:45])[C@H:27]([CH2:35][C:36]1[CH:41]=[C:40]([Cl:42])[C:39]([OH:43])=[C:38]([Cl:44])[CH:37]=1)[NH:28][C:29](=[O:34])[C:30]([F:33])([F:32])[F:31].CN(C)C=O>CC(C)=O>[CH3:24][O:25][C:26](=[O:45])[C@H:27]([CH2:35][C:36]1[CH:37]=[C:38]([Cl:44])[C:39]([O:43][CH2:8][C:9]2[C:14]3[O:15][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[C:40]([Cl:42])[CH:41]=1)[NH:28][C:29](=[O:34])[C:30]([F:33])([F:31])[F:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 145149507-Chloromethyl-2-phenylbenzofuranHCID 150239503,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester

Product 1

HCID 865983223,5-dichloro-N-trifluoroacetyl-O-[(2-phenylbenzo[b]fur-7-yl)methyl]-L-tyrosine methyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (180 mg, 1.30 mmol) and 7-chloromethyl-2-phenylbenzo[b]furan. (171 mg, 0.705 mmol) were added in turn to a solution of 3,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester (221 mg, 0.614 mmol) in acetone (3 ml) with stirring under ice cooling and the mixture was stirred under argon atmosphere at the same temperature for 5 hrs. Dimethylformamide (2 ml) and n-tetrabutylammonium iodide (23 mg, 0.062 mmol) were added to the mixture and stirred at room temperature for 21 hrs. The reaction mixture was poured into ice-water (50 ml) and extracted with ethyl acetate. The extract was washed with water and saturated brine solution in turn and dried. The solvent was distilled off under reduced pressure. The residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=5) to give 3,5-dichloro-N-trifluoroacetyl-O-[(2-phenylbenzo[b]fur-7-yl)methyl]-L-tyrosine methyl ester (182 mg, 52%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred under argon atmosphere at the same temperature for 5 hrs
  2. stirringstirred at room temperature for 21 hrs
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine solution in turn
  5. customdried
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=5)

Sources & evidence

ORD record
ord-96e43520adb648cfbeb70e20f4f044ff
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

Loading…