L-Phenylalanine → HCID 66787548, compound

HRID 1474590Notes

Reaction equation

HRID 1474590 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22]O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.O1CCOCC1>O1CCOCC1>[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][O:11][C:10](=[O:12])[C@H:2]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH2:1])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6140L-PhenylalanineHCID 76889BenzenebutanolHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 66787548HCID 66787548, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.03 g of phenylalanine and 22.8 g of 4-phenyl-1-butanol were added to 17 mL of 1,4-dioxane, 17 mL of 4N—HCl/1,4-dioxane was added thereto, and the reaction solution was stirred at room temperature for 4 days. The reaction solution was filtered and the filtrate was added with 450 mL of diethyl ether, and stirred at room temperature for 1.5 hours. The deposit was taken by filtration, washed with 50 mL of diethyl ether, and then dried under vacuum, thereby to give 5.90 g of Compound 16.

Workup

  1. additionwas added
  2. filtrationThe reaction solution was filtered
  3. additionthe filtrate was added with 450 mL of diethyl ether
  4. stirringstirred at room temperature for 1.5 hours
  5. filtrationThe deposit was taken by filtration
  6. washwashed with 50 mL of diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-8841f012c3b149488defb6ffd3eabc95
Source dataset
uspto-grants-2015_04
Patent number
US09018323B2

Reaction notes

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