1-Hydroxybenzotriazole → HCID 89835604、化合物

HRID 2277084ノート

反応式

HRID 2277084 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[C:24](O)=[O:25])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:27]([O:31][C:32](=[O:44])[NH:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=1[CH2:42][NH2:43])([CH3:30])([CH3:29])[CH3:28].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[C:24](=[O:25])[NH:43][CH2:42][C:36]3[CH:37]=[C:38]([Cl:41])[CH:39]=[CH:40][C:35]=3[CH2:34][NH:33][C:32]([O:31][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:44])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 9830421-{[(9H-Fluoren-9-yl)methoxy]carbonyl}piperidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11149921Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

生成物 1

HCID 89835604HCID 89835604、化合物収率 76.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of crude (S)-1-[{(9H-Fluoren-9-yl)methoxy}carbonyl]piperidine-2-carboxylic acid (0.75 g, 2.21 mmol), tert-butyl[2-(aminomethyl)-4-chlorobenzyl]carbamate (0.52 g, 1.93 mmol), HOBT (0.26 g, 1.93 mmol), and EDC.HCl (0.48 g, 2.51 mmol) in DMF (5 mL) was stirred under nitrogen at room temperature for 16 h. The reaction mixture was quenched with water (20 mL) and diluted with EtOAc (50 mL). The organic layer was washed sequentially with saturated aqueous NaHCO3 solution (50 mL) and brine solution (50 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile:water) to afford the title compound (0.89 g) as a white solid.

後処理

  1. customThe reaction mixture was quenched with water (20 mL)
  2. additiondiluted with EtOAc (50 mL)
  3. washThe organic layer was washed sequentially with saturated aqueous NaHCO3 solution (50 mL) and brine solution (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile:water)

出典と根拠

ORDレコード
ord-700c9a2e625c4353b5a785cf5d3996f7
出典データセット
uspto-grants-2015_09
特許番号
US09133147B2

反応ノート

読み込み中…