Tryptamine hydrochloride → Kumujian A

HRID 628666

Reaction equation

HRID 628666 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[CH2:14]([O:16][C:17](=[O:20])[CH:18]=O)[CH3:15]>C(O)C.C1(C)C=CC=CC=1>[CH2:14]([O:16][C:17]([C:18]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH:4]=[CH:3][N:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:20])[CH3:15]

Participants

5

Reactant 2

HCID 67652Tryptamine hydrochlorideHCID 70211Ethyl oxoacetate

Product 1

HCID 11701473Kumujian A

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a suspension of tryptamine hydrochloride (2.00 g, 10.17 mmol) in ethanol (25 mL) was added a solution of glyoxylic acid ethyl ester (3.12 g, 15.26 mmol) in toluene (50% v/v) at 0° C. After the reaction mixture was stirred overnight at ambient temperature, the solvent was removed under reduced pressure. The resulting residue was treated with saturated aqueous sodium bicarbonate. The product was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product was used in the next step without further purification.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe resulting residue was treated with saturated aqueous sodium bicarbonate
  3. extractionThe product was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-3b814fa746c84ca6bacc617ccb47992d
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Linked notes

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