tert-Butyl carbazate → N1-(tert-butoxycarbonyl)-N2-(4-biphenylylmethyl)hydrazine

HRID 1043979노트

반응식

HRID 1043979 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[NH:25][NH2:26]>CN(C=O)C>[C:29]([O:28][C:24]([NH:25][NH:26][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

참가 물질

5

반응물 3

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

생성물 1

HCID 10637828N1-(tert-butoxycarbonyl)-N2-(4-biphenylylmethyl)hydrazine수율 70.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(Bromomethyl)biphenyl (2.0 g, 8.1 mmol, 1.0 eq.) and DIPEA (1.4 mL, 1.0 eq.) were dissolved in DMF (40.0 mL). t-Butyl carbazate (2.1 g, 16.2 mmol, 2.0 eq.) was added and the mixture was stirred at room temperature overnight. The mixture was partially concentrated, and the residue was partitioned between EtOAc and a saturated aqueous NaHCO3 solution. The EtOAc layer was then dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (0-60% EtOAc/hexanes with 0.5% DIPEA) to yield compound 1, N′-biphenyl-4-ylmethyl-hydrazinecarboxylic acid t-butyl ester (1.7 g).

후처리

  1. concentrationThe mixture was partially concentrated
  2. customthe residue was partitioned between EtOAc
  3. dry with materialThe EtOAc layer was then dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (0-60% EtOAc/hexanes with 0.5% DIPEA)

출처 및 근거

ORD 기록
ord-c5a870ffd848454c9efcb41a44c92624
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563512B2

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