Benzyl Alcohol → Benzyl 3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionate

HRID 1533275ノート

反応式

HRID 1533275 の反応式
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:14]([O:18][C:19]([N:21]1[CH:25]=[C:24]([CH2:26][CH:27]([C:39]2[CH:44]=[CH:43][C:42]3[O:45][CH2:46][O:47][C:41]=3[CH:40]=2)[C:28](N2[C@@H](C(C)C)COC2=O)=[O:29])[N:23]=[C:22]1[CH2:48][CH2:49][CH2:50][CH3:51])=[O:20])([CH3:17])([CH3:16])[CH3:15]>O1CCCC1>[C:14]([O:18][C:19]([N:21]1[CH:25]=[C:24]([CH2:26][CH:27]([C:39]2[CH:44]=[CH:43][C:42]3[O:45][CH2:46][O:47][C:41]=3[CH:40]=2)[C:28]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:29])[N:23]=[C:22]1[CH2:48][CH2:49][CH2:50][CH3:51])=[O:20])([CH3:17])([CH3:16])[CH3:15]

参加物

5

反応物 3

HCID 244Benzyl AlcoholHCID 56994932(4S)-3-[3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionyl]-4-isopropyloxazolidin-2-oneHCID 178418339Butyllithium

生成物 1

HCID 22012330Benzyl 3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionate収率 78.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of benzyl alcohol (1.29 g) in tetrahydrofuran (60 ml) was added dropwise n-butyl lithium (6.6 ml, 1.6M n-hexane solution) at 2-8° C. and the mixture was stirred for 20 minutes. A solution of (4S)-3-[3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionyl]-4-isopropyloxazolidin-2-one (4.86 g) was added dropwise to the mixture and the resulting solution was stirred at 2° C. for 2 hours. The reaction was quenched with saturated ammonium chloride aqueous solution, and then the solution was extracted with ethyl acetate. The organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of the solvents afforded a crude product. The crude product was purified by a silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1) to give benzyl 3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionate (2R:2S=1:4) (3.67 g) as a slightly yellow oil.

後処理

  1. stirringthe resulting solution was stirred at 2° C. for 2 hours
  2. customThe reaction was quenched with saturated ammonium chloride aqueous solution
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine
  5. customDrying
  6. filtrationfiltering
  7. customremoval of the solvents
  8. customafforded a crude product
  9. customThe crude product was purified by a silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-a79a41b725ca41f0ae9e9cca164c8d93
出典データセット
uspto-grants-2001_03
特許番号
US06207686B1

反応ノート

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