L-Phenylalanine → HCID 66991917, compound

HRID 556458Notes

Reaction equation

HRID 556458 reaction equation
[OH-].[Na+].[CH:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([NH2:14])[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.Cl[C:16]1([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26]>O1CCOCC1>[Cl:25][C:21]1[CH:20]=[C:19]2[C:24]([C:16]([NH:14][CH:10]([CH2:9][C:6]3[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=3)[C:11]([OH:13])=[O:12])([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=3)[C:17](=[O:26])[NH:18]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6140L-PhenylalanineHCID 14798Sodium HydroxideHCID 57507304HCID 57507304, compound

Product 1

HCID 66991917HCID 66991917, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To an aqueous solution of NaOH (1N, 10 mL) at 0° C. was added L-2-amino-3-phenyl-propionic acid (1.47 g, 8.92 mmol), followed by the addition of solution of 3,6-dichloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (3 g, 8.1 mmol) in 1,4-dioxane (3 mL). After the reaction mixture was stirred at 0° C. for 4 h, the solution was concentrated and extracted with diethyl ether. The organic layer was dried over Na2SO4, filtered and concentrated.

Workup

  1. concentrationthe solution was concentrated
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c4b96074d0d34ef38d4fd92f93d2b248
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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