Dabco → HCID 13001869、化合物

HRID 2286326ノート

反応式

HRID 2286326 の反応式
[C:1]([O:5][C:6]([N:8]([CH3:28])[C@H:9]([C:25]([OH:27])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:40][C@@H:41]([C:43]([O:45]CC1C=CC=CC=1)=[O:44])[CH3:42].C1N2CCN(CC2)C1.C1CCC(N=C=NC2CCCCC2)CC1>CCOCC.CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH3:28])[C@H:9]([C:25]([NH:40][C@@H:41]([C:43]([OH:45])=[O:44])[CH3:42])=[O:27])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 5

HCID 9237DabcoHCID 10868DicyclohexylcarbodiimideHCID 85570p-ToluenesulfonateHCID 726857D-Alanine, phenylmethyl esterHCID 7010604Boc-N-Me-Tyr(Bzl)-OH

生成物 1

HCID 13001869HCID 13001869、化合物収率 99%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To 30 ml. of DMF were added 2.73 grams (7.1 mmoles) of Nα -t-butyloxycarbonyl-Nα -methyl-O-benzyl-L-tyrosine (prepared by acidification of 3.6 grams of the product from Part A and extraction into ether). The solution was cooled to 0° C., and 2.26 grams (7.1 mmoles) of the tosylate salt of D-alanine, benzyl ester, were added followed by 0.794 grams (7.1 mmoles) of triethylenediamine. The mixture was stirred at 0° C. for five minutes, and 0.96 grams of HBT and 1.46 grams (7.1 mmoles) of DCC were added. The mixture was stirred at 0° C. for two hours and then at room temperature for 24 hours. The mixture then was cooled to 0° C. and filtered. The filtrate was concentrated in vacuo to an oil, and then the oil was dissolved in ethyl acetate and extracted successively with 1 N aqueous sodium bicarbonate, water, 1.5 N citric acid, and water. The organic phase was dried over magnesium sulfate and concentrated in vacuo to an oil. The oil was dissolved in 60 ml. of ethanol, and 1.5 grams of 5% palladium on carbon were added to the mixture as a water slurry. Nitrogen was bubbled into the reaction mixture through a gas dispersion tube for five minutes followed by hydrogen gas for 24 hours. The mixture was flushed with nitrogen, and the catalyst was removed by filtration. The reaction mixture was concentrated in vacuo to an amorphous solid to give 2.5 grams (99 percent) of the title compound.

後処理

  1. stirringThe mixture was stirred at 0° C. for two hours
  2. waitat room temperature for 24 hours
  3. temperatureThe mixture then was cooled to 0° C.
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo to an oil
  6. dissolutionthe oil was dissolved in ethyl acetate
  7. extractionextracted successively with 1 N aqueous sodium bicarbonate, water, 1.5 N citric acid, and water
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. concentrationconcentrated in vacuo to an oil
  10. dissolutionThe oil was dissolved in 60 ml
  11. additionof ethanol, and 1.5 grams of 5% palladium on carbon were added to the mixture as a water slurry
  12. customNitrogen was bubbled into the reaction mixture through a gas dispersion tube for five minutes
  13. waitfollowed by hydrogen gas for 24 hours
  14. customThe mixture was flushed with nitrogen
  15. customthe catalyst was removed by filtration
  16. concentrationThe reaction mixture was concentrated in vacuo to an amorphous solid

出典と根拠

ORDレコード
ord-f3af852b73624bc2b0021ab4a2029bd7
出典データセット
uspto-grants-1981_05
特許番号
US04265808

反応ノート

読み込み中…