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

HRID 80582
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HRID 80582 반응식
[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
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참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1140
Toluene
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b88d4aaf11f545d5a6b814da4935e75e
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846660B2

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