Water → HCID 90281952, compound

HRID 1497509Notes

Reaction equation

HRID 1497509 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[CH:25]=[CH2:26].O>CS(C)=O>[C:29]([O:28][C:24](=[O:27])[CH2:25][CH2:26][NH:2][C@H:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15458tert-Butyl acrylateHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Product 1

HCID 90281952HCID 90281952, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of tert-butyl L-phenylalaninate hydrochloride (800 mg) in dimethyl sulfoxide (3.20 mL) were added potassium carbonate (429 mg) and tert-butyl acrylate (0.901 mL), followed by stirring at 150° C. for 1 hour under microwave. After cooling to room temperature, water was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl N-(3-tert-butoxy-3-oxopropyl)-L-phenylalaninate (266 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2468dee88d814db18cce85e43342a28c
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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