Dicyclohexylcarbodiimide → Benzyl L-leucinate

HRID 1418325

反応式

HRID 1418325 の反応式
[CH3:1][CH:2]([CH2:4][C@@H:5]([NH:9]C(OC(C)(C)C)=O)[C:6]([OH:8])=[O:7])[CH3:3].[CH2:17]1[CH:21]2[CH:22]3C(=O)N(O)C(=O)[CH:23]3[CH:18]1[CH:19]=[CH:20]2.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CCOC(C)=O>[NH2:9][C@H:5]([C:6]([O:8][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7])[CH2:4][CH:2]([CH3:1])[CH3:3]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 637604tert-Butoxycarbonyl-D-leucine

生成物 1

HCID 6451313Benzyl L-leucinate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

pTos (21.6 g) was dissolved in DMF (100 ml), and the solution was cooled with ice. TEA (7.7 ml) and Boc-D-Leu-ONB (prepared from Boc-D-Leu--OH. H2O (12.5 g), HONB (9.86 g) and DCC (11.4 g) were added thereto, followed by stirring overnight. The resulting DCU was separated by filtration, and the filtrate was concentrated to obtain a residue. The residue was dissolved in AcOEt, and the resulting solution was washed with 4% aqueous NaHCO3 and 10% aqueous citric acid. After washing with water, the solution was dried with Na2SO4 and concentrated. Ether was added to the resulting residue to separate out a precipitate, which was collected by filtration.

後処理

  1. temperaturethe solution was cooled with ice
  2. additionwere added
  3. customThe resulting DCU was separated by filtration
  4. concentrationthe filtrate was concentrated
  5. customto obtain a residue
  6. washthe resulting solution was washed with 4% aqueous NaHCO3 and 10% aqueous citric acid
  7. washAfter washing with water
  8. dry with materialthe solution was dried with Na2SO4
  9. concentrationconcentrated
  10. additionEther was added to the resulting residue
  11. customto separate out a precipitate, which
  12. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-8e0604e70dc24857806d6d9ce38d0ab4
出典データセット
uspto-grants-1999_03
特許番号
US05883075

関連ノート

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