Trifluoroacetic acid → N-Fmoc,2-(trans-Dec-4-en-1-ylamino)acetaldehyde

HRID 898640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898640
C[O:2][CH:3](OC)[CH2:4][N:5]([CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:6]([O:8][CH2:9][CH:10]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7].C(O)(C(F)(F)F)=O>O>[C:6]([N:5]([CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:4][CH:3]=[O:2])([O:8][CH2:9][CH:10]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 21966301N-Fmoc-2-(trans-Dec-4-en-1-ylamino)acetaldehyde dimethyl acetal

Produkt 1

HCID 21966305N-Fmoc,2-(trans-Dec-4-en-1-ylamino)acetaldehydeAusbeute 115 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

N-Fmoc-2-(trans-Dec-4-en-1-ylamino)acetaldehyde dimethyl acetal (5 g, 10.7 mmol) was mixed with 30 mL of TFA and stirred at room temperature for 30 minutes. The reaction was poured into water (140 mL) and centrifuged to obtain a clear oil. The supernatant was decanted and the oil was mixed with 40 mL of water and centrifuged again. The supernatant was again decanted and the oil was dissolved in dichloromethane (100 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to obtain 5.2 g (12.3 mmol) of N-Fmoc-2-(trans-Dec-4-en-1-ylamino)acetaldehyde as a clear oil.

Aufarbeitung

  1. customto obtain a clear oil
  2. customThe supernatant was decanted
  3. additionthe oil was mixed with 40 mL of water
  4. customThe supernatant was again decanted
  5. dissolutionthe oil was dissolved in dichloromethane (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b100e4c0b0ab4e24b0cd5e457e62ff58
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351791B2

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