Triethylamine → HCID 66739291, compound

HRID 2066338Notes

Reaction equation

HRID 2066338 reaction equation
Cl.C(O)(=O)CCC.[NH2:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:20]([OH:22])(=[O:21])[CH2:9][CH2:10][CH2:11][CH2:19][CH2:18][CH2:17][CH3:16].[NH2:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 66738995HCID 66738995, compound

Product 1

HCID 66739291HCID 66739291, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 g of tryptophan butanoate hydrochloride salt (commercially available from Sigma-Aldrich, St. Louis, Mo. (www.sima-aldrich.com)) was suspended in 100 mL of dichloromethane and 3 ml of triethylamine was added to the suspension with stirring. Stirring was continued for 15 min and the resulting solution was transferred to a separatory funnel. The organic solution was washed twice with 25 mL of water followed by 25 mL of saturated aqueous sodium bicarbonate. The organic layer was then dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide tryptophan octanoate. The structure was confirmed using mass spectroscopy.

Workup

  1. stirringStirring
  2. customthe resulting solution was transferred to a separatory funnel
  3. washThe organic solution was washed twice with 25 mL of water
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0d8b786b1eb4338b92913235f7edd33
Source dataset
uspto-grants-2012_10
Patent number
US08293253B2

Reaction notes

Loading…