Pentanamide, 2-amino-3-methyl-N-(phenylmethyl)-, (2S,3S)- synthesis
- Product Name:Pentanamide, 2-amino-3-methyl-N-(phenylmethyl)-, (2S,3S)-
- CAS Number:129253-02-7
- Molecular formula:C13H20N2O
- Molecular Weight:220.31
134015-91-1
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Yield:129253-02-7 88%
Reaction Conditions:
with hydrogen bromide;acetic acid at 20;Schlenk technique;
Steps:
General procedure for the deprotection of N-Cbz-L-aminoamides 6a-h
General procedure: General procedure for the deprotection of N-Cbz-L-aminoamides 6a-h: The N-Cbz-amino amide was treated with a solution of HBr/AcOH (33%) and the mixture was stirred at room temperature untilCO2 evolution ceased. At this point, dry diethyl ether was added tothe clear solution, which led to the deposition of a precipitate. Thiswas filtered and washed with additional ether and dissolved indistilled water; the resulting solution was extracted with chloroform(310 mL). Solid NaOH was then added up to a pH value of 12and the resulting solution was saturated with NaCl and extractedwith chloroform (310 mL). The organic phase was dried overanhydrous MgSO4 and evaporated under vacuum to obtain a whitesolid 4.4.5. (2S,3S)-2-Amino-N-benzyl-3-methylpentanamide (6e).Yield88%; mp164.1e166.0 C; [a]D20 7.2 (c 0.1, MeOH); ESIMSm/z221.1 (MH); IR (KBr) nmax: 3290, 2935, 1953, 1684,1532, 1257 cm1; 1H NMR (500 MHz, CDCl3) dH: 0.92e1.01 (m,6H, CH3) 1.58e1.61 (m, 2H, CH2), 1.87e1.96 (m, 1H, CH), 3.73 (d,1H, J5.4 Hz, CH*), 4.34e4.50 (dd, 2H, J14.4 Hz, NHCH2Ph),7.28e7.33 (m, 5H, AreH); 13C NMR (125 MHz, CDCl3) dC: 10.5,14.0, 24.3, 36.9, 43.1, 57.9, 127.4, 128.3, 128.5, 138.5, 168.1; Anal.Calcd for C13H20N2O: C, 70.87; H, 9.15; N, 12.72. Found: C, 70.98;H, 9.19; N, 12.78
References:
Escorihuela, Jorge;Altava, Belen;Burguete, M. Isabel;Luis, Santiago V. [Tetrahedron,2013,vol. 69,# 2,p. 551 - 558]
3160-59-6
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3391-99-9
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13139-16-7
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