Dimethylamine → Benzyloxycarbonyl-(L)-Phenylalanine Dimethylamide

HRID 246889

Reaktionsgleichung

Reaktionsgleichung von HRID 246889
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:24]1[C:28](=O)CC[C:25]1=O.C1(N=C=NC2CCCCC2)CCCCC1.CNC>C(Cl)(Cl)Cl>[CH3:25][N:24]([CH3:28])[C:20](=[O:22])[C@H:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 10868DicyclohexylcarbodiimideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 80170N-Hydroxysuccinimide

Produkt 1

HCID 12653775Benzyloxycarbonyl-(L)-Phenylalanine Dimethylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

20 mmoles (5.99 grams) of N-benzyloxycarbonyl-(L)-phenylalanine and 24 mmoles (2.76 grams) of N-hydroxysuccinimide are dissolved in 30 ml of chloroform and treated under ice cooling and stirring with 22 mmoles (4.34 grams) of dicyclohexylcarbodiimide dissolved in about 10 ml of chloroform. After 10 minutes stirring the mixture was cooled in an ice-salt bath to -10° C. and 20 mmoles (0.90 grams) of condensed, dry dimethylamine (boiling point +7° C.) added. Stirring was carried out for 24 hours, whereby the cooling bath was allowed to slowly melt. The precipitate formed was filtered off and the filtrate washed successively with each 20 ml 2N hydrochloric acid, saturated NaHCO3 solution and water. After drying over sodium sulfate and drawing off the solvent in a vacuum there was obtained an oily product. It was distilled at 240° C. air bath temperature in a high vacuum (10-4Torr). Colorless, very viscous oil.

Aufarbeitung

  1. additiontreated under ice cooling
  2. additionadded
  3. stirringStirring
  4. waitwas carried out for 24 hours
  5. customThe precipitate formed
  6. filtrationwas filtered off
  7. washthe filtrate washed successively with each 20 ml 2N hydrochloric acid, saturated NaHCO3 solution and water
  8. dry with materialAfter drying over sodium sulfate
  9. customwas obtained an oily product
  10. distillationIt was distilled at 240° C. air bath temperature in a high vacuum (10-4Torr)

Quellen und Nachweise

ORD-Eintrag
ord-f61a8e4d50c649568b872ba7912c66a0
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04704464

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