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

HRID 2212466Notes

Reaction equation

HRID 2212466 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-388eda1e197e4735ace61d772dfd54b1
Source dataset
uspto-grants-2006_09
Patent number
US07101964B2

Reaction notes

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