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Dicyclohexylcarbodiimide → [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid methyl ester

HRID 476693
ノート
印刷プレビュー

反応式

HRID 476693 の反応式
[CH3:1][O:2][P:3]([CH2:17][CH:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:19](O)=[O:20])([CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])=[O:4].[CH3:26][NH:27][C:28](=[O:35])[C@H:29]([CH2:31][CH:32]([CH3:34])[CH3:33])[NH2:30].O[C:37]1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:1][O:2][P:3]([CH2:17][CH:18]([C:19](=[O:20])[NH:30][C@H:29]([C:28](=[O:35])[NH:27][CH3:26])[CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:22][C:23]([CH3:37])([CH3:24])[CH3:25])([CH2:5][N:6]1[C:7](=[O:16])[C:8]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]2[C:10]1=[O:11])=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 11672684(2S)-2-amino-N,4-dimethylpentanamideHCID 200630192(RS)-[[(RS)-(methoxy)(phthalimidomethyl)phosphinyl]methyl]-4-methylvaleric acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 54363570[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid methyl ester
収率 80.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3.0 g of 2(RS)-[[(RS)-(methoxy)(phthalimidomethyl)phosphinyl]methyl]-4-methylvaleric acid were dissolved in 50 ml of tetrahydrofuran and 1.65 g of L-leucine N-methylamide and 2.2 g of hydroxybenzotriazole were added while stirring. After all of the solids had dissolved, 2.02 g of N,N'-dicyclohexylcarbodiimide were added and the mixture was stirred at room temperature overnight. The tetrahydrofuran was removed by evaporation, the residue was triturated with 100 ml of ethyl acetate and the mixture was filtered in order to remove dicyclohexylurea. The filtrate was washed twice with 50 ml of saturated sodium hydrogen carbonate solution each time, dried over anhydrous sodium sulfate and evaporated to give a yellow gum. This gum was purified by flash chromatography on silica gel using 5% methanol in ethyl acetate for the elution. There were obtained 3.32 g of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid methyl ester in the form of a white foam.

後処理

  1. dissolutionAfter all of the solids had dissolved
  2. stirringthe mixture was stirred at room temperature overnight
  3. customThe tetrahydrofuran was removed by evaporation
  4. customthe residue was triturated with 100 ml of ethyl acetate
  5. filtrationthe mixture was filtered in order
  6. customto remove dicyclohexylurea
  7. washThe filtrate was washed twice with 50 ml of saturated sodium hydrogen carbonate solution each time
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated
  10. customto give a yellow gum
  11. customThis gum was purified by flash chromatography on silica gel using 5% methanol in ethyl acetate for the elution

出典と根拠

ORDレコード
ord-cf38cf9fa7da41dea8bef27cc9ac6185
出典データセット
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04885283

反応ノート

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