4-Nitrobenzyl bromide → N-(t-butyldimethylsilyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-hydroxypropyl]-azetidin-2-one

HRID 371289ノート

反応式

HRID 371289 の反応式
[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]([OH:18])[CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:9]1=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1)([O-:22])=[O:21]>C(N(CC)CC)C>[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]([OH:18])[CH2:14][C:15]([O:17][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=2)=[O:16])[CH2:10][C:9]1=[O:19])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 660114-Nitrobenzyl bromideHCID 15136308N-(t-butyldimethylsilyl)-4-(3-carboxy-2-hydroxypropyl)-azetidin-2-one

生成物 1

HCID 12848994N-(t-butyldimethylsilyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-hydroxypropyl]-azetidin-2-one

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

The crude carboxylic acid is suspended in anhydrous acetonitrate (150 ml) and treated with p-nitrobenzyl bromide (7.56 g, 35 mμol) and triethylamine (4.9 ml, 35 mμol). The resulting solution is kept at room temperature for 2 days and then in a refrigerator for 3 days. The reddish orange solution is evaporated under vacuum and the residue shaken with ethyl acetate (100 ml, 2×50 ml) and filtered to remove triethylammonium bromide. The ethyl acetate filtrate is washed with water (3×100 ml) and brine, dried with magnesium sulfate, filtered, and evaporated under vacuum to an amber oil (13.62 g). Crystallization from diethyl ether affords N-(t-butyldimethylsilyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-hydroxypropyl]-azetidin-2-one (6.84 g) as an off-white powder. Chromatography of the mother liquors on a silica gel column using 1:1 toluene-ethyl acetate as eluting solvent affords addition product (3.14 g) as an oil which solidifies.

後処理

  1. waitin a refrigerator for 3 days
  2. customThe reddish orange solution is evaporated under vacuum
  3. filtrationfiltered
  4. customto remove triethylammonium bromide
  5. washThe ethyl acetate filtrate is washed with water (3×100 ml) and brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum to an amber oil (13.62 g)
  9. customCrystallization from diethyl ether

出典と根拠

ORDレコード
ord-20643c4863ce4d0fbd20d71c5bb12be2
出典データセット
uspto-grants-1985_07
特許番号
US04530841

反応ノート

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