ChemicalBook CAS DataBase List Isopropyl L-phenylalaninate hydrochloride(L-phenylalanine

Isopropyl L-phenylalaninate hydrochloride(L-phenylalanine synthesis

7synthesis methods

Product Name:Isopropyl L-phenylalaninate hydrochloride(L-phenylalanine
CAS Number:18934-70-8
Molecular formula:C12H17NO2
Molecular Weight:207.2689

L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methylethyl ester

247178-99-0
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Isopropyl L-phenylalaninate hydrochloride(L-phenylalanine

18934-70-8
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Yield:18934-70-8 82%

Reaction Conditions:

with trifluoroacetic acid in dichloromethane at 0 - 25; for 4 h;

Steps:

6.2 Step 2: isopropyl L-phenylalaninate

To a solution of isopropyl (tert-butoxycarbonyi)-L-phenylalaninate (22.7 g, 73.8 mmol) In DCM (120 mL) was added TFA (40 mL, 519 mmol) at 0 °C. The resulting mixture was stirred at 25 °C for 4 h. LCMS showed the reaction was completed. The reaction mixture was concentrated under reduced pressure. The residue was neutralized with NH₄HCQ₃(20 mL), diluted with water (200 mL) and extracted with DCM (3 * 200 mL). Then the combined organic layers were washed with brine (100 mL), dried over NaaS04, filtered and concentrated. The residue was purified by silica gel chromatography (DCM/MeOH = 10/1) to give isopropyl L-phenyiaianinate (12.5 g, 60.3 mmol, 82 % yield) as a yellow oil. LCMS (M+H) = 208.0; Retention time (0.1% TFA) = 1.13 min.

References:

WO2022/182604,2022,A1 Location in patent:Page/Page column 73; 74

63-91-2 Synthesis