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L-N-Boc-phenylalanineamide synthesis
- Product Name:L-N-Boc-phenylalanineamide
- CAS Number:88463-18-7
- Molecular formula:C14H20N2O3
- Molecular Weight:264.32
![N-(tert-Butoxycarbonyl)-L-phenylalanine](/CAS/GIF/13734-34-4.gif)
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Yield:88463-18-7 100%
Reaction Conditions:
Stage #1: N-tert-butoxycarbonyl-L-phenylalaninewith chloroformic acid ethyl ester;triethylamine in tetrahydrofuran at 0; for 0.5 h;
Stage #2: with ammonia hydrochloride in tetrahydrofuran;lithium hydroxide monohydrate at 0; for 0.5 h;
Steps:
4.3.5 4.3. Typical procedure for the primary amidation of Cbz-l-Phe-OH 3a with NH4Cl
General procedure: To a colorless solution of 150mg (0.50mmol) of Cbz-L-Phe-OH 3a in 10mL of THF were added 67μL (0.70mmol, 1.4equiv) of ClCO2Et and 209μL (1.5mmol, 3.0equiv) of Et3N at 0°C.
After stirring for 30min at 0°C, 0.75 ml of a 1.0M aqueous solution of NH4Cl (0.75mmol, 1.5equiv) were added at 0°C to the colorless suspension.
The mixture was stirred for 30min at 0°C and 5mL of H2O was added to the resulted mixture.
The colorless clear solution was extracted with 30mL of EtOAc and the aqueous layer was extracted with 20mL of EtOAc.
The organic layers were combined, washed with 5mL of brine, and dried over anhydrous MgSO4.
The crude product was chromatographed on silica gel with EtOAc to afford 129mg (86% yield) of Cbz-L-Phe-NH2 4a. 4.3.5
Boc-l-Phe-NH2 4c
132?mg (quant.); >99% ee; colorless solid; mp: 142-144?°C; [α]23D?=?+12.9 (c 1.00, MeOH); 1H NMR (400?MHz, DMSO-d6): δ 1.30 (s, 9H, CH3 *3), 2.72 (dd, J?=?10.2, 13.8?Hz, 1H, CHAC6H5), 2.95 (dd, J?=?4.4, 13.8?Hz, 1H, CHBC6H5), 4.08 (ddd, J?=?4.4, 8.8, 10.2?Hz, 1H, CH), 6.81 (d, J?=?8.8?Hz, 1H, NHCH), 7.01 (br, 1H, CONHA), 7.16-7.21, 7.24-7.28 (m, m, 1H, 4H, C6H5), 7.37 (br, 1H, CONHB); 13C NMR (100?MHz, DMSO-d6): δ 28.1, 37.5, 55.6, 77.9, 126.1, 128.0, 129.2, 138.3, 155.2, 173.6; IR (KBr, vmax/cm-1)?=?3390 (CONH), 3346 (CONH), 3192 (CONH), 1684 (CON), 1660 (CON); HRMS (ESI-TOF): Calcd for C14H20N2O3Na (M+Na)+: 287.1366, found: 287.1351; The enantiomeric ratio was determined by HPLC (Chiralcel AD: hexane/2-propanol?=?95/5): Tr 20.7?min.
References:
Ezawa, Tetsuya;Kawashima, Yuya;Noguchi, Takuya;Jung, Seunghee;Imai, Nobuyuki [Tetrahedron Asymmetry,2017,vol. 28,# 12,p. 1690 - 1699]
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24424-99-5
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![H-PHE-NH2](/CAS/GIF/5241-58-7.gif)
5241-58-7
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![L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, anhydride with ethyl hydrogen carbonate](/CAS/20211123/GIF/119153-87-6.gif)
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