Acetone → 1-(Tert-butoxycarbonyl)-4-[2,6-difluoro-4-(benzyloxycarbonyl)aminophenyl]piperazine

HRID 77429

반응식

HRID 77429 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([NH2:21])=[CH:16][C:15]=2[F:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)=O.C(=O)(O)[O-].[Na+].Cl[C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34]>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]([F:22])=[CH:16][C:17]([NH:21][C:33]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:34])=[CH:18][C:19]=2[F:20])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 180AcetoneHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 45925741tert-Butyl 4-(4-amino-2,6-difluorophenyl)piperazine-1-carboxylate2회

생성물 1

HCID 214626171-(Tert-butoxycarbonyl)-4-[2,6-difluoro-4-(benzyloxycarbonyl)aminophenyl]piperazine수율 90%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

To a solution of 4-(4-amino-2,6-difluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (Intermediate III) (25 g, 0.08 mol), in 1:1 acetone:water (300 mL) was added sodium bicarbonate (15.1 g, 0.18 mol). The resulting solution was cooled to 0° C. and benzyl chloroformate (40 mL, 0.24 mol, 50% solution in toluene) was added dropwise. The reaction mixture was stirred at r.t. and progress of the reaction was monitored by TLC. On completion, solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (500 mL). The organic layer was washed with water (2×50 mL), brine (100 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 2:3 ethyl acetate:Pet. ether) to provide title compound (32 g, 90%) as off white solid.

후처리

  1. customOn completion, solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (500 mL)
  3. washThe organic layer was washed with water (2×50 mL), brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, 2:3 ethyl acetate:Pet. ether)

출처 및 근거

ORD 기록
ord-30f02fab636b452cb88bf9d04bc20bcf
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841306B2

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