L-Phenylalanine → HCID 11069180, compound

HRID 1464859Notes

Reaction equation

HRID 1464859 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH2:13][C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:25]1([Se:31][CH2:32][CH2:33]O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C[O:38][CH2:37][CH2:36]1>C(OCC)(=O)C>[C:25]1([Se:31][CH2:32][CH2:33][O:23][C:22](=[O:24])[C@H:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:13][C:37](=[O:38])[CH3:36])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6140L-PhenylalanineHCID 8028TetrahydrofuranHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11030856Ethanol, 2-(phenylseleno)-

Product 1

HCID 11069180HCID 11069180, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 50 ml round bottomed flask, 2.55 g (13.3 mmol) of 1-(3-dimethylamino propyl)-3-ethyl carbodiimide hydrochloride and 1.7 g of (8.2 mmol) phenylalanine were added to a solution of 1.87 g (9.3 mmol) of 2-(phenylseleno)ethanol in 20 ml of THF. The reaction mixture was then stirred for 12 hours at room temperature. The mixture was then diluted with 50 ml of ethyl acetate and extracted with 50 ml of a 0.5 M HCl solution. The organic phase was dried over sodium sulfate, filtered, and the solvent was removed in vacuo. Purification by column chromatography (PE:EE=2:1) yielded 2.9 g (91% of th., 98% of lit.) of a yellowish liquid.

Workup

  1. extractionextracted with 50 ml of a 0.5 M HCl solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customPurification by column chromatography (PE:EE=2:1)
  6. customyielded 2.9 g (91% of th., 98% of lit.) of a yellowish liquid

Sources & evidence

ORD record
ord-6f795c9c7dd7420494421229fb03b2f9
Source dataset
uspto-grants-2015_04
Patent number
US08999323B2

Reaction notes

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