HCID 67363471, 화합물 → HCID 67364561, 화합물

HRID 1516181노트

반응식

HRID 1516181 반응식
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[N+:15]([O-])=O)[CH3:2].[H][H]>C(OCC)(=O)C.[Pd].[Br-].[Zn+2].[Br-]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([CH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[NH2:15])[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH3:2]

참가 물질

6

반응물 2

HCID 67363471HCID 67363471, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67364561HCID 67364561, 화합물수율 95.5%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 10421208Zinc bromide촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of [tert-butoxycarbonyl-(5-chloro-2-nitro-benzyl)-amino]-acetic acid ethyl ester (69.0 g, 0.186 mol) in ethyl acetate (1200 ml) was added zinc bromide (8.5 g, 0.037 mol). The reaction mixture was purged with argon after 15 min. After addition of the palladium catalyst (10% on activated charcoal, 7.9 g, 0.0074 mol) the mixture was hydrogenated at ambient pressure during a period of ca. 48 h until ca. 13 l of hydrogen gas had been consumed. The catalyst was removed by filtration and the filtrate was washed with two portions of saturated aqueous sodium bicarbonate solution and brine, each. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (60.6 g, 95.5%) as yellow waxy solid. MS m/e: 343 (M+H+).

후처리

  1. customThe reaction mixture was purged with argon after 15 min
  2. customhad been consumed
  3. customThe catalyst was removed by filtration
  4. washthe filtrate was washed with two portions of saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ec5ea9947a5d4f90aa5ab7974097e9be
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227458B2

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