3-Iodobenzylamine → 1-tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-iodobenzyl)amino]propylcarbamate

HRID 857259ノート

反応式

HRID 857259 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]2[CH2:13][O:12]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[I:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27].FC1C=C(C[C@H](NC(=O)OCC2C=CC=CC=2)[C@H]2CO2)C=C(F)C=1>C(O)(C)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]([OH:12])[CH2:13][NH:27][CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[C:23]([I:22])[CH:24]=1

参加物

5

反応物 3

HCID 970123-IodobenzylamineHCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamateHCID 10131699HCID 10131699、化合物

生成物 1

HCID 161093481-tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-iodobenzyl)amino]propylcarbamate

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

tert-Butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, PREPARATION 3, 1.75 g, 5.8 mmole) is mixed with isopropanol (30 ml). The reaction flask is charged with 3-iodobenzylamine (VI). The reaction mixture is heated to reflux for 45 minutes, HPLC analysis indicates complete disappearance of the epoxide (V). The reaction mixture is concentrated under reduced pressure and the residue is partitioned between ethyl acetate (150 ml) and aqueous hydrochloric acid (3%, 35 ml). The organic phase is separated and washed with aqueous hydrochloric acid (3%, 20 ml), bicarbonate, saline and dried over sodium sulfate. Concentration under reduced pressure gives the title compound, M+H=535.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 45 minutes
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customthe residue is partitioned between ethyl acetate (150 ml) and aqueous hydrochloric acid (3%, 35 ml)
  5. customThe organic phase is separated
  6. washwashed with aqueous hydrochloric acid (3%, 20 ml), bicarbonate, saline
  7. dry with materialdried over sodium sulfate
  8. concentrationConcentration under reduced pressure

出典と根拠

ORDレコード
ord-881a014510ca4361b09454574dfd49ed
出典データセット
uspto-grants-2006_12
特許番号
US07144897B2

反応ノート

読み込み中…