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

HRID 2272632ノート

反応式

HRID 2272632 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-000e2c8fdc6f41f0864f8adbe0f35c89
出典データセット
uspto-grants-2015_09
特許番号
US09120758B2

反応ノート

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