Trifluoroacetic acid → (6R)-2-chlorophenyl 6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-1,4-diazepane-1-carboxylate

HRID 80582Notes

Reaction equation

HRID 80582 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:41][CH3:42])=[C:6]([CH:40]=1)[CH2:7][C@H:8]1[C:14](=[O:15])[N:13]([C:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[O:17])[CH2:12][C:11](=[O:26])[N:10](CC2C(OC)=CC(OC)=CC=2OC)[CH2:9]1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:41][CH3:42])=[C:6]([CH:40]=1)[CH2:7][C@H:8]1[C:14](=[O:15])[N:13]([C:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[O:17])[CH2:12][C:11](=[O:26])[NH:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 66935304(6R)-2-chlorophenyl 6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-carboxylate

Product 1

HCID 86672188(6R)-2-chlorophenyl 6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-1,4-diazepane-1-carboxylateYield 56.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the compound S141C described in WO 06-059801A, that is, (6R)-2-chlorophenyl 6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-carboxylate (996 mg), anisole (1.75 ml) and trifluoroacetic acid (10 ml) were added, and the mixture was stirred at room temperature for 4.5 hours. The reaction solution was diluted with toluene and concentrated in vacuo. This operation was repeated two times and excessive anisole was distilled off under reduced pressure of a vacuum pump. To the residue, ethyl acetate was added. The precipitated solid was collected by filtration to obtain the title compound (396 mg). Furthermore, the filtrate was concentrated, and the residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=2/1 to 1/3) to obtain the title compound (198 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. distillationwas distilled off under reduced pressure of a vacuum pump
  3. additionTo the residue, ethyl acetate was added
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-b88d4aaf11f545d5a6b814da4935e75e
Source dataset
uspto-grants-2014_09
Patent number
US08846660B2

Reaction notes

Loading…