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Ammonium Chloride → (R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone

HRID 1050556
ノート
印刷プレビュー

反応式

HRID 1050556 の反応式
CON(C)[C:4](=[O:28])[C@H:5]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH3:30][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[CH2:13]([O:12][C:10]([NH:9][CH2:8][CH2:7][CH2:6][C@@H:5]([NH:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C:4](=[O:28])[CH3:30])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 118114437N-methoxy-N-methyl-(R)-5-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)pentanamideHCID 178418689HCID 178418689、化合物

生成物 1

HCID 98005910(R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

N-Methoxy-N-methyl-(R)-5-(Benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-pentanamide (305) (10 g, 24 mmol) was dissolved in THF (250 mL) and the solution was cooled to −30° C. in a dry-ice acetone bath. MeMgBr (3M in Et2O, 123 mL, 369 mmol) was added drop-wise over 30 minutes. The bath temperature was slowly allowed to increase to 0° C. and then was maintained at 0° C. until TLC showed no further reaction progress (˜80-90% complete). Saturated NH4Cl (aq) was then slowly added to the reaction mixture at 0° C. and the THF was removed under reduced pressure. The resulting aqueous solution was then extracted with EtOAc and the extracts were washed with water and then brine. The residue was then purified by column chromatography (EtOAc/hexanes) to give (R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone (306), (6.5 g, 18 mmol, 75% yield).

後処理

  1. temperatureto increase to 0° C.
  2. temperaturewas maintained at 0° C. until TLC
  3. customthe THF was removed under reduced pressure
  4. extractionThe resulting aqueous solution was then extracted with EtOAc
  5. washthe extracts were washed with water
  6. customThe residue was then purified by column chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-96670990d15e4bcc90f8296974acea66
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09382246B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート