Ammonium Chloride → (4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester

HRID 1019753노트

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HRID 1019753 반응식
[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([O:18][CH3:19])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CO.[Zn]>[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([O:18][CH3:19])[CH:10]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 67256007Benzyl-(3-methoxy-4-nitro-benzyl)-carbamic acid tert-butyl ester

생성물 1

HCID 21034184(4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester수율 85.3%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

To a solution of benzyl-(3-methoxy-4-nitro-benzyl)-carbamic acid tert-butyl ester (1.2 g, 3.22 mmol) in methanol (24 mL) was added a saturated aqueous solution of NH4Cl (24 mL) and zinc powder (1.05 g 16.11 mmol). The reaction was heated to 60° C. for 2 hours then the reaction mass was cooled to room temperature and filtered through celite. The solvents were removed under reduced pressure then the residue was partitioned between EtOAc (24 mL) and water (24 mL). The separated aqueous layer was extracted with EtOAc (12 ml), and then the combined organic extracts were washed with water (24 mL), brine (24 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (0.94 g, 85%).

후처리

  1. temperaturethe reaction mass was cooled to room temperature
  2. filtrationfiltered through celite
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was partitioned between EtOAc (24 mL) and water (24 mL)
  5. extractionThe separated aqueous layer was extracted with EtOAc (12 ml)
  6. washthe combined organic extracts were washed with water (24 mL), brine (24 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9ffaba7b644846b1b1568756e4d7b2a6
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716287B2

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