Diisopropylethylamine → Ethyl 2-(4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylcarbonylamino)-3-methylphenoxy)acetate

HRID 1459413노트

반응식

HRID 1459413 반응식
[CH3:1][C:2]([CH3:22])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].Cl.[NH2:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:27][C:26]=1[CH3:38].C1CCN(C(Cl)=[N+]2CCCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:3][C:2]([CH3:22])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:24][C:25]3[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:27][C:26]=3[CH3:38])=[O:18])=[CH:20][CH:21]=2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 27955084-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acidHCID 15429165Chlorodipiperidinocarbenium hexafluorophosphateHCID 70346506Acetic acid,(4-amino-3-methylphenoxy)-,ethyl ester hydrochloride

생성물 1

HCID 54494373Ethyl 2-(4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylcarbonylamino)-3-methylphenoxy)acetate수율 100.1%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

To a 100 mL round bottomed flask with a stirring bar and an argon inlet was added 4-(4-(1,1-dimethylethoxycarbonyl) piperazinyl)benzoic acid (0.75 g, 2.45 mmol), ethyl 4-amino-3-methylphenoxyacetate hydrochloride (0.60 g, 2.45 mmol), chloro-N,N,N',N',-bis(pentamethylene)formamidinium hexafluorophosphate (0.97 g, 2.69 mmol), and CH2Cl2 (30 mL). This mixture was cooled in an ice bath and diisopropylethylamine (1.74 mL, 10.0 mmol) was added. The ice bath was allowed to expire and the solution was stirred at ambient temperature for 48 h. The solution was diluted with CHCl3 and washed with 10% aqueous citric acid, saturated aqueous NaHCO3, and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an oil. This material was chromatographed on 75 g of silica gel using 50% EtOAc-hexane as eluant. There was obtained 1.22 g (100%) of ethyl 2-(4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylcarbonylamino)-3-methylphenoxy)acetate as a crystalline solid.

후처리

  1. temperatureThis mixture was cooled in an ice bath
  2. washwashed with 10% aqueous citric acid, saturated aqueous NaHCO3, and brine
  3. customDrying
  4. filtration(MgSO4), filtration and removal of the solvent in vacuo
  5. customgave an oil
  6. customThis material was chromatographed on 75 g of silica gel using 50% EtOAc-hexane as eluant

출처 및 근거

ORD 기록
ord-cfcac2ee88514dd5a9b52f876acab767
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05854245

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