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1,5-Hexadiene → 8-(N-benzyloxycarbonylamino)-4-bromomethyl-2-formylamino-oct-3-enoic acid methyl ester

HRID 487445
ノート
印刷プレビュー

反応式

HRID 487445 の反応式
[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:24][CH:25]=[O:26])[CH:5](O)[C:6](=[CH2:22])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].C=CCCC=C.S(Br)([Br:36])=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:24][CH:25]=[O:26])[CH:5]=[C:6]([CH2:22][Br:36])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]
参加物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 115981,5-HexadieneHCID 68176Thionyl bromideHCID 216926188-(N-benzyloxycarbonylamino)-2-formylamino-3-hydroxy-4-methylene-octanoic acid methyl ester

生成物 1

HCID 544393678-(N-benzyloxycarbonylamino)-4-bromomethyl-2-formylamino-oct-3-enoic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 2.46 g (6.5 mmol) of 8-(N-benzyloxycarbonylamino)-2-formylamino-3-hydroxy-4-methylene-octanoic acid methyl ester in 25 ml of tetrahydrofuran there are added 5.5 ml (46 mmol) of hexa-1,5-diene and then, dropwise at -50°, 2.6 ml (32.5 mmol) of thionyl bromide. The mixture is stirred at from 0° to 5° for 2 hours, poured into 25 ml of ice-cold saturated sodium hydrogen carbonate solution and extracted twice with 20 ml of methylene chloride each time. The organic phase is washed with 10 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated to dryness by evaporation. The resulting oil is purified by chromatography on silica gel with hexane/ethyl acetate (3:1). 8-(N-benzyloxycarbonylamino)-4-bromomethyl-2-formylamino-oct-3-enoic acid methyl ester is obtained.

後処理

  1. customdropwise at -50°
  2. extractionextracted twice with 20 ml of methylene chloride each time
  3. washThe organic phase is washed with 10 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness by evaporation
  6. customThe resulting oil is purified by chromatography on silica gel with hexane/ethyl acetate (3:1)

出典と根拠

ORDレコード
ord-2fe920b95e4f44c59f46378a7a39cec0
出典データセット
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05294734

反応ノート

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