Triphenylphosphine → Benzyloxycarbonyl-2-[1-(2,4-dimethoxybenzyl)-2,5-dioxopyrrolidin-3-yl] glycine methyl ester

HRID 358301

反応式

HRID 358301 の反応式
[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[CH3:24][O:25][C:26]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:27]=1[CH2:28]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH:16]1[CH2:20][C:19](=[O:21])[N:18]([CH2:28][C:27]2[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:26]=2[O:25][CH3:24])[C:17]1=[O:22])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 817502,4-Dimethoxybenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13105389Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine methyl ester

生成物 1

HCID 20449787Benzyloxycarbonyl-2-[1-(2,4-dimethoxybenzyl)-2,5-dioxopyrrolidin-3-yl] glycine methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In 100 ml of tetrahydrofuran were dissolved 3.2 g of benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine methyl ester, 1.8 g of 2,4-dimethoxybenzyl alcohol and 3.9 g of triphenylphosphine and under ice-cooling 2 ml of diethyl azodicarboxylate was added. The mixture was stirred at room temperature for one hour and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with 5% sodium hydrogen carbonate and 10% phosphoric acid in that order and dried over sodium sulfate. The solution was concentrated under reduced pressure and the concentrate was chromatographed on a silica gel column, elution being carried out with toluene-ethyl acetate (7:3). The eluate was concentrated under reduced pressure and to the residue was added petroleum ether. The precipitate was collected by filtration and dried. Yield 1.2 g.

後処理

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with 5% sodium hydrogen carbonate and 10% phosphoric acid in that order
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated under reduced pressure
  7. customthe concentrate was chromatographed on a silica gel column, elution
  8. concentrationThe eluate was concentrated under reduced pressure and to the residue
  9. additionwas added petroleum ether
  10. filtrationThe precipitate was collected by filtration
  11. customdried

出典と根拠

ORDレコード
ord-7f80ed19ce8148eea873befe7a1827be
出典データセット
uspto-grants-1984_08
特許番号
US04465844

関連ノート

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