Imidazole → (R)-tert-butyl 3-(4-(1H-imidazol-1-yl)phenyl)-1-amino-1-oxopropan-2-ylcarbamate

HRID 2201132Notes

Reaction equation

HRID 2201132 reaction equation
[NH2:1][C:2](=[O:20])[C@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[N:21]1([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C@@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:2]([NH2:1])=[O:20])=[CH:6][CH:7]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 67516556(R)-tert-butyl 1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 67515389(R)-tert-butyl 3-(4-(1H-imidazol-1-yl)phenyl)-1-amino-1-oxopropan-2-ylcarbamateYield 79.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of (R)-tert-butyl 1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamate (370 mg, 0.948 mmol), imidazole (85 mg, 1.25 mmol), 8-hydroxyquinoline (30 mg, 0.206 mmol), K2CO3 (150 mg, 1.08 mmol) and CuI (20 mg, 0.105 mmol) in DMSO (4 mL) was degassed with argon, then was stirred at 130 C for 18 h. The mixture was purified by HPLC to give (R)-tert-butyl 3-(4-(1H-imidazol-1-yl)phenyl)-1-amino-1-oxopropan-2-ylcarbamate (250 mg).

Workup

  1. customwas degassed with argon
  2. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-9e697e8df77a4d49a350567dfbddca80
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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